I'm very skeptical of this idea. I don't mean to spread "negative energy" or flame but, may I be frank?

Walking it through:

Let's start with the straw-man that I'm a small single shop and don't want CC processing. Cashierlive will take me as a customer for $50/month - but I can buy a robust cash register that will last years for less than that and I'll probably save more than $50/month using my own in-house inventory management system even if I wind up having to enter journal tape and receipt data into my PC manually. On top of that, the used cash register I buy will likely be a more robust solution.

Suppose I'm that same dinky shop but now I want to add CC processing. There already exists a competitive market for low-acquisition-cost, fee-based CC processing - just go into any corner liquor store in a big city. I can either add a service fee to CC and debit card purchases, or set a minimum purchase price for card usage and adjust my retail prices slightly. (Which is right depends on the nature of my products and my customers.)

Suppose I'm still a single shop but larger and more sophisticated. I want integration of POS with inventory management. I want CC processing. If I'm setting up for the first time to achieve that state I have to drop a decent chunk of change on HW and I damn sure want to have competing offers from CC processing companies. Yet with cashierlive I'm locked into cashierlive's CC processing partners and any subsidy I'm getting on software or hardware looks like chump change in my larger budget.

The higher up the chain my business goes, the less attractive it is to (a) trust cashier live to protect my data; (b) trust cashier live to to remain in business; (c) trust cashier live to keep up with me in feature demands; (d) trust cashier live to avoid massive attacks on their servers; (e) trust that cashier live isn't down when I need to collect reports to file taxes; etc.

As a larger, more sophisticated customer - all those unknowns and risks greatly outweigh the relatively modest cost savings.

What about if I have multiple stores and am really attracted to the cross-site inventory management features? Or like the "access anywhere" features for reporting. At that point I'm sophisticated and flush enough that I can probably do better on my own - with bespoke software if I have to.

The low end of the market has plenty of reasons to find a simpler, more robust, cost competitive solution in existing markets. The high end has every reason to run, not walk, from the kind of centralization of control and purchasing decisions that cashier live implies.

Cashier Live as a business seems to be essentially a value-added broker of CC processing services. In that sense, it competes directly against the IT/POS consultant that my local accounting firm uses - the guy who actually comes into my shop and connects devices and strings wire. Cashier Live is competing against that with on-line training videos and a help line - which is weak. It's especially weak since, regardless, I still have to hire my local accounting firm.

Swapping out my "small business perspective" hat for my "engineer with VC sensitivities" hat: the centralization of data and services proposed by cashier live are just nuts. It creates a massive and precarious single point of failure in direct proportion to the number of customers it acquires and the number of transactions it processes. Asked to comment on the technology I would be conscious bound to speak out against it. Asked to invest, I would have to decline.

BUT: HOW TO FIX IT!!!!

Web-based POS, inventory mgt. etc. is a fine idea provided (as noted in other comments) it's hardened against interruptions of net connectivity and avoids centralization. All of the problems I listed above have to do with the unreasonable centralization of cashier live's model: centralization of choice about CC processing agents; centralization of choice about software features; centralization of choice about database structure, backup-policy, etc.; .....

I think cashier live would have a chance if it polished up its code, released it under GPL, partnered with accounting firms instead of directly CC processing firms, and went into the premium fee support / consulting business while learning to franchise sales to put qualified reps on the floor of customer's shops to hook things up.

I have a hunch that cashier live grew out of doing some bespoke work and then trying to turn that into a commodity service "web 2.0 style". Perhaps the better course would be to learn how to do bespoke work at scale, for a premium.

It would even be OK for cashier live to resell hosting for the web service provided that hosting weren't centralized and the customer had the option of finding their own hosting.