<PAGE>   1

                                                               EXHIBIT 10.101


                       FLOOD INSURANCE SERVICES AGREEMENT


         THIS FLOOD INSURANCE SERVICES AGREEMENT ("Agreement") is entered into
by and between INSURANCE MANAGEMENT SOLUTIONS, INC. ("Vendor"), a corporation
organized and existing under the laws of Florida with its principal place of
business located at 360 Central Avenue, St. Petersburg, Florida 33702, and
Middlesex Mutual Assurance Company ("Company"), an insurer existing under the
laws of Connecticut with its principal place of business located at 213 Court
Street, Middletown, CT 06457-0891.

         WHEREAS, the Federal Emergency Management Agency ("FEMA") and the
Federal Insurance Administration ("FIA") administer the National Flood
Insurance Program ("NFIP") and Company is an insurance company duly licensed to
write flood insurance in the state or states to which this Agreement pertains
and is approved by FIA to act as a Write Your Own Flood Carrier ("WYO Carrier")
under the Write Your Own Flood Insurance Program ("WYO Flood Program"), a
program offered under the NFIP; and

         WHEREAS, Vendor has been designated by FIA as a "qualified performer"
for the provision of services to WYO Carriers under the NFIP; and

         WHEREAS, Company wishes to engage the services of Vendor to administer
certain of Company's obligations as a WYO Carrier in the state(s) set forth
herein.

         NOW THEREFORE, IN CONSIDERATION OF the mutual covenants and agreements
hereinafter set forth, the parties hereto do covenant and agree as follows:

I.      AUTHORITY OF VENDOR:

        A.  Appointment - Company hereby appoints Vendor to supervise and
            administer its WYO Flood Program in those states ("Applicable
            States") specified in the attached "Territory Schedule", attached
            to and hereto made a part of this Agreement. Vendor hereby accepts
            such appointment, and the grant of authority, and agrees to carry
            out the resulting duties and responsibilities to the best of its
            ability, knowledge, skill, and judgment, and in accordance with the
            highest reasonably attainable standards of quality generally
            utilized in the insurance and data processing industries.

        B.  Authority - Company hereby grants Vendor the authority to act for
            and on behalf of Company in matters required for Vendor to properly
            supervise and conduct the handling of the aforesaid WYO Flood
            Program, including the authority to collect and remit premiums,
            process applications and other forms, issue policies, and process
            claims, all in a manner consistent with, pursuant to and as
            authorized by the provisions of the National Flood Insurance Act of
            1968 (as amended), the regulations of the NFIP, FIA, FEMA and the
            terms of this Agreement.

II.     SPECIFIC RESPONSIBILITIES OF VENDOR:

        A.  Policy Administration: - Vendor shall administer Company's WYO
            Flood Program policies ("WYO Policy", or the plural, "WYO
            Policies") and in accordance therewith shall be responsible for the
            following policy administration functions: compliance with
            community eligibility/rating criteria; policyholder eligibility
            determination; WYO Policy issuance; WYO Policy endorsements; WYO
            Policy cancellations; WYO Policy correspondence; payment of agents'
            commissions on Company's behalf; and, the receipt, recording,
            control, timely deposit, and disbursements of premium funds in
            connection with the foregoing, all in accordance with the WYO Flood
            Program Financial Control Plan ("Financial 





<PAGE>   2


            Control Plan") requirements established by the FIA. Further, Vendor
            shall reply to written and telephone inquiries from policyholders
            and/or producers regarding any WYO Policy administered pursuant to
            this Agreement.

        B.  Full Claim Service - Company shall have responsibility for the
            administration and processing of WYO Policy claims ("Claim") under
            this Agreement. Vendor shall provide "Full Claim Service", which
            shall be defined as processing and administering a Claim from the
            Claim's inception until closing. The Claim shall be processed and
            administered in accordance with the following procedures:

            1.  Processing. Vendor shall provide Claims processing in
                accordance with the Arrangement and the Financial Control Plan.
                Vendor may also rely on information and direction contained in
                the WYO Flood Program Claims Manual, the FEMA Adjuster Manual,
                the Flood Insurance (Agent's) Manual, the standard flood
                insurance policy, the WYO Operational Overview, and/or other
                WYO Flood Program instructional material.

            2.  Catastrophe Office. A catastrophe team may be engaged at the
                discretion of the Vendor to provide Claims support. Vendor
                shall coordinate activities and shall provide information to
                the FIA or its designee whenever a flood insurance catastrophe
                office is established.

        C.  Statistical Reporting - Vendor shall prepare and submit, to FIA,
            monthly financial and statistical reports, reconciliations,
            certifications, and statistical tapes on Company's behalf, in
            accordance with WYO Flood Program Accounting Procedures and the
            Transaction Record Reporting and Processing Plan ("TRRP Plan").
            Vendor shall submit copies of all monthly reports to the Company.

        D.  Company Agents - Vendor shall provide to each Company Agent
            appointed under this Agreement, a limited license to use Vendor's
            FloodWriter(C)(TM) software program, and a current flood zone
            determination for any WYO Policy application submitted pursuant to
            this Agreement. Further, excluding records required to be
            maintained by Company in accordance with the Flood Writer(C)(TM)
            software license, Vendor shall keep appropriate records, in
            conformity with Internal Revenue Services regulations, for the
            purpose of preparing 1099 reports for Company Agent's commissions
            and Adjuster's fees paid by Vendor on behalf of Company. The
            expense for the above services has been incorporated into the
            Vendor's Monthly Service Fee.

        E.  Time Standards - Vendor shall use it best efforts to adhere to
            certain time standards for performance, as may be outlined and
            amended from time to time within the FEMA/FIA Financial
            Assistance/Subsidy Arrangement ("Arrangement").

III.    PREMIUM COLLECTION AND ARRANGEMENT

        A.  Banking Arrangement - Vendor and Company shall establish banking
            arrangements which comply with the Arrangement and other WYO Flood
            Program requirements, and which will provide for the establishment
            of a NFIP restricted account ("Restricted Account") with Company as
            custodian, and a FEMA letter of credit ("Letter of Credit"), with
            additional accounts as needed to facilitate operations, all in
            conformity with FEMA/FIA guidelines. Company shall grant specific
            Vendor employees check-signing authority on any Restricted Account
            and the authority to initiate appropriate drawdowns against
            Company's Letter of Credit, in order for Vendor to act on Company's
            behalf in making 




                                       2

<PAGE>   3

            disbursements for Company liabilities established by the
            Arrangement, the WYO Flood Program, and this Agreement. All such
            authorizations shall be in writing and may be revoked, amended or
            modified at any time by Company upon thirty (30) days advance
            written notice to Vendor.

        B.  Premium Remittance - Vendor shall be liable to the FIA for any
            premiums Vendor has received on WYO Flood Program business written
            under this Agreement. Vendor shall establish procedures for a
            timely deposit and remittance of funds to the U.S. Treasury via
            authorized automatic clearinghouse mechanism. Gross premium
            collected by Vendor, for WYO Flood Program business written under
            this Agreement, shall be remitted to the FIA by Vendor net of the
            established NFIP Allowable Expenses. "Allowable Expenses" shall
            mean a WYO Carrier's operating and administrative expenses.

        C.  Financial Data - Vendor shall maintain supporting documentation for
            all bank accounts over which it has authority. At least monthly,
            Vendor shall prepare financial data, by state, reflecting all
            debits and credits with respect to WYO Flood Program business
            written pursuant to this Agreement, including agents' commissions
            and Vendor's Servicing Fees paid, during the preceding quarter.

IV.      COMPANY ACCESS TO RECORDS

         Vendor agrees to permit Company or its duly appointed representatives,
         during the term of this Agreement, the right to visit, inspect,
         examine, copy, verify and audit, at Vendor's offices, any of the
         accounts, files, documents, books, reports and other records in
         possession or control of Vendor relating directly to the WYO Flood
         Program business covered by this Agreement. Such access shall be given
         during reasonable business hours and upon ten (10) days prior written
         notice to Vendor.

         Furthermore, at Company's expense, Vendor shall conduct a biennial
         audit of any and all WYO Flood Program business written by Company
         pursuant to this Agreement. To minimize the expense incurred by
         Company for such biennial audit, Vendor shall select an auditor,
         subject to Company's approval, and shall coordinate the biennial
         audit.

V.       EXPENSES AND FEES

        A.  Monthly Service Fee - Company shall pay Vendor a monthly servicing
            fee ("Servicing Fee") as specified in the "Servicing Fee Schedule",
            attached to and hereto made a part of this Agreement.

        B.  Claims Administration Fee - In addition to the above Servicing Fee,
            Company shall pay Vendor a claim administration fee ("Claim
            Administration Fee") as specified in the "Claims Administration Fee
            Schedule", attached hereto and made a part of this Agreement.

        C.  Additional Expenses - In accordance with the Arrangement, Company
            shall be liable for operating, administrative and production
            expenses, including but not limited to any State premium taxes,
            agents' commissions, or any other expense of whatever nature
            incurred by the Company in the performance of its obligations under
            the Arrangement.

        D.  Vendor Expenses - In consideration of the Servicing Fees and Claims
            Administration Fees paid to Vendor, Vendor shall pay the general
            expenses of processing the WYO Flood Program Policies, including
            those of policy 




                                       3

<PAGE>   4

            administration, cash management, claims processing and financial
            and transactional reporting.

        E.  WYO Flood Program Reimbursements - Any WYO Flood Program
            Reimbursements made pursuant to the Arrangement, including, but not
            limited to, those for the unallocated loss adjustments, the
            allocated loss adjustments, and for approved special allocated loss
            expenses, shall be payable to Vendor upon receipt by Company.

        F.  Marketing Goals - Company shall maintain responsibility for any
            risk, or shall be entitled to any reward, that may be associated
            with achieving or failing to achieve any marketing goal set by the
            FIA or FEMA.


VI.      ADDITIONAL SERVICES AND FEES

        A.  FULL BOOK FLOOD ZONE DETERMINATIONS - Upon Company's request, Vendor
            shall provide a flood zone determination on each of, or a portion
            of, Company's homeowners policies for a fee of $10.00 per policy. 

        B.  Agent or Company Training - Upon Company request, Vendor will
            provide one training session per quarter, or four training sessions
            per year, to Company or Company's agents. Company shall provide the
            training facility. Additional requests for training outside of the
            4 provided within this Agreement, will be  charged at $125 per
            day plus reasonable per diem and travel expenses incurred.

        C.  Marketing Material - Company may use Vendor's previously developed
            marketing or promotional materials, which Vendor may customize and
            produce for Company at Company's expense.

        D.  Additional Fees and Service - Additional services not defined in
            this Agreement may be provided as mutually agreed upon between the
            Company and Vendor in writing.

VII.     CONFIDENTIALITY OF DATA AND INFORMATION

        A.  Confidential and Proprietary Information - Vendor and Company
            acknowledge that any and all information concerning the other's
            business is confidential and proprietary information ("Confidential
            Information") and neither party shall permit the duplication, use,
            or disclosure of any such Confidential Information to any person,
            other than its own employees, agents or representatives who must
            have such information for the performance of obligations hereunder,
            unless such duplication, use, or disclosure is specifically
            authorized in writing by the other party. Confidential Information
            is not meant to include any information which: at the time of
            disclosure is generally known to the public and/or the insurance
            industry prior to the disclosure.

        B.  Trademarks, Service Marks, Trade Names - Neither party shall use or
            duplicate the name(s), trademark(s), service mark(s), or trade
            name(s) (whether registered or not) of the other party in public
            releases or advertising or in any other manner unless such use or
            duplication is specifically authorized in writing by the other
            party, except that Vendor may include Company's name in a list of
            clients/customers without such authorization.

        C.  Agreement Terms - Neither party shall disclose information as to
            specific terms of this Agreement, in particular any details about
            the work performed or the 




                                       4

<PAGE>   5

            Service Fees or Claims Administration Fees paid, without prior
            written consent of the other party.

        D.  Company's Records - Vendor shall maintain system integrity and data
            security necessary to protect Company's records and data from loss
            and damage and to protect against unauthorized disclosure of
            Company's Confidential Information as described in section VII (A)
            above.

        E.  Public Disclosure - The disclosure restrictions provided in this
            section shall be extinguished at the time and to the extent that
            the Confidential Information becomes generally available to the
            public domain without the fault of either Vendor or Company.

VIII.    COMMENCEMENT AND TERMINATION

        A.  Term of Agreement - This Agreement shall become effective on the
            date that this document is executed by Company and by Vendor and
            shall have a minimum initial term of thirty six (36) full calendar
            months unless terminated earlier pursuant to Section 8.C of this
            Agreement. The Agreement shall be renewed and extended after
            conclusion of the initial term for an additional renewal term of
            thirty six (36) months unless otherwise terminated pursuant to
            Section(s) 8.B and 8.C of this Agreement.

        B.  Termination Without Cause - This Agreement may be terminated,
            without cause, at any time after the initial thirty six (36) month
            term by either party upon written notice of termination to the
            other, not less than ninety (90) days prior to the Termination
            Date.

        C.  Termination for Cause - Any party may immediately terminate this
            Agreement for cause upon written notice to the other party in the
            event of:

            1.  Bankruptcy, receivership, of either party, regardless of
                whether any of these occur voluntarily or involuntarily; or

            2.  Failure by any party to fulfill a material obligation under
                this Agreement, provided that such party has been notified in
                writing of such failure and such failure continues without cure
                for a period of ninety (90) days after written notice thereof.

        D.  Accounting - Upon termination of this Agreement, Vendor shall fully
            account to Company for all of its responsibilities and activities
            pursuant to this Agreement.


IX.      LIABILITY

        A.  Limit of Liability - In no event shall Vendor's liability for
            breach of this Agreement or any of its provisions exceed the
            Company's liability to FEMA in connection with the WYO Flood
            Program. Vendor shall not be liable for any lost profits, business
            goodwill, or other consequential, punitive, special or incidental
            damages incurred by Company.

        B.  Vendor Indemnification - Vendor shall indemnify, defend and hold
            harmless Company, its officers, and directors from any liability,
            cost, loss, fine, penalty, claim, demand, damage or expense,
            including attorney's fees, incurred as a direct result of any act,
            error or omission by Vendor, or incurred as a result of any
            material breach of Vendor's obligations under this Agreement.
            Vendor's 




                                       5

<PAGE>   6

            indemnification under this paragraph shall be in accordance with
            the limitations set forth in this Agreement.

        C.  Company Indemnification - Company shall indemnify, defend and hold
            harmless Vendor, its officers, and directors from any liability,
            cost, loss, fine, penalty, claim, demand, damage or expense,
            including attorney's fees, incurred as a direct result of any act,
            error or omission by Company or incurred as a result of any
            material breach of Company's obligations under this Agreement.
            Company's indemnification under this paragraph shall be in
            accordance with the limitations set forth in this Agreement.

        D.  Notice of Claim - All parties agree to promptly give the other
            notice upon being notified or becoming aware of an allegation or
            claim which could give rise to a claim under this section.

X.       GENERAL AGREEMENTS

        A.  Applicable Law - This Agreement in all matters arising thereunder
            shall be governed by and determined in accordance with the laws of
            the State of Florida. Venue for any actions arising hereunder shall
            be in a State court of competent jurisdiction in Pinellas County,
            Florida.

        B.  Entire Agreement - This Agreement, and any exhibits, schedules or
            addenda attached hereto, contain all of the prior oral and/or
            previously written agreements, representations, and arrangements
            between the parties hereto. There are no representations or
            warranties other than those set forth herein. No change or
            modification of this Agreement shall be valid unless the same shall
            be in writing and signed by all of the parties hereto. All
            schedules, addendum of any kind, or attachments to this Agreement
            shall be made a part of this Agreement and shall be subject to all
            terms and conditions of this Agreement.

        C.  Attorney's Fees - If either party should bring a Court action
            alleging breach of this Agreement or seeking to enforce, rescind,
            renounce, declare void or terminate this Agreement or any
            provisions thereof, the prevailing party shall be entitled to
            recover all of its legal expenses, including reasonable attorney's
            fees and costs (including legal expenses for any appeals taken),
            and to have the same awarded as part of the judgment in the
            proceeding in which such legal expenses and attorney's fees were
            incurred.

        D.  Company Warranties - Company warrants that it has entered into an
            agreement with FEMA pursuant to which it is authorized to issue WYO
            Policies, and that it is licensed to engage in the insurance
            business in all jurisdictions in which it has duly authorized
            Vendor to issue WYO Policies or other insurance coverage in the
            Company's name. Further, Company warrants to Vendor that it will
            comply with the laws of the state or states covered by this
            Agreement and with the rules and regulations of all regulatory
            authorities having jurisdiction over Company's activities, and
            shall, whenever necessary, maintain at its own expense all required
            licenses to transact business in such states.

        E.  Vendor Warranties - Vendor warrants to Company that it is duly
            authorized and incorporated to transact the business of servicing
            insurance companies. Further, Vendor warrants to Company that it
            will comply with the laws of the state or states covered by this
            Agreement and with the rules and regulations of all regulatory
            authorities having jurisdiction over Vendor's activities, and
            shall, 




                                       6

<PAGE>   7

            whenever necessary, maintain at its own expense all required
            licenses to transact business in such states.

        F.  Invalidation - Should any part of this Agreement for any reason be
            declared invalid, such decision shall not effect the validity of
            any remaining portion, which remaining portion shall remain in full
            force and effect as if the Agreement had been executed with the
            invalid portion thereof eliminated. It is, therefore, declared the
            intention of the parties hereto that each of them will have
            executed the remaining portion of this Agreement without including
            therein any such part, parts or portion which may, for any reason,
            be hereafter declared void.

        G.  Construction of Agreement - The parties acknowledge that each party
            and its counsel have reviewed and revised this Agreement and that
            the normal rule of construction to the effect that any ambiguities
            are to be resolved against the drafting party shall not be employed
            in the interpretation of this Agreement or any amendments or
            exhibits hereto.

        H.  Miscellaneous - Words of a gender used in this Agreement shall be
            held to include any other gender, the words in a singular number
            held to include the plural, when the sentence so requires. Section
            headings are intended for purposes of description only and shall
            not be used for purposes of interpretation of this Agreement.

        I.  Notices - Any and all notices, designations, consents, offers,
            acceptances, or any other communication provided for herein shall
            be given in writing by hand delivery, by overnight carrier, by
            registered or certified mail or by facsimile transmission and shall
            be addressed as follows:

            As to Company:     Middlesex Mutual Assurance Company
                               213 Court St.
                               Middletown, CT 06457-0891
                               Fax Number: (860) 638-5093
                               Attention:  Bill Sheridan, Senior Vice President


            As to Vendor:      Insurance Management Solutions, Inc. 
                               360 Central Avenue
                               St. Petersburg, FL 33701
                               Fax Number: (813) 823-6518
                               Attention:  Kathy Batson, Senior Vice President

                  Notices sent by hand delivery shall be deemed effective on
                  the date of hand delivery. Notices sent by overnight carrier
                  shall be deemed effective on the next business day after
                  being placed into the hands of the overnight carrier. Notices
                  sent by registered or certified mail shall be deemed
                  effective on the third business day after being deposited
                  into the post office. Notices sent by facsimile transmission
                  shall be deemed to be effective on day when sent if sent
                  prior to 4:30 p.m. (the time being determined by the time
                  zone of the recipient) otherwise they shall be deemed
                  effective on the next business day.




                                       7

<PAGE>   8

IN WITNESS WHEREOF, the parties hereto by their respective duly authorized
representatives have executed this Agreement this 23rd day of October, 1998. 
The term of this contract will begin upon completion of the data conversion on 
or before February 1, 1999.


"Vendor":                                   "Company":

INSURANCE MANAGEMENT SOLUTIONS, INC.        MIDDLESEX MUTUAL ASSURANCE COMPANY

By: /s/ Jeffrey S. Bragg                    By: /s/ William R. Sheridan
   --------------------------------            -------------------------------

As its: COO                                 As its: Chief Underwriting Officer -
       ----------------------------                 SVP.   
                                                    ---------------------------

Date:   10/22/98                            Date:   10/23/98
     ------------------------------              -----------------------------




                                       8