Well, after a significant amount of investigation, I've decided the source of leaks is not the air conditioner.  The 32 year old tile roof is the problem.  It has to be replaced. 

My next dilema is the fact that the home is a duplex.  The adjoining home owner says his roof is not leaking and does not need to be replaced.  I have credible information from the former owner's housekeeper that his roof has leaked in the past, but the HOA says they can't make him replace his roof. 

I will have to pay extra to have my side of the roof replaced because the tiles presently on the roof are no longer made and my new roof must match his existing roof.  Further, the tiles I'll have to buy must be painted to match his roof, since the new product does not come in a similar color. 

I think I'll have to replace the plywood decking and attic insulation.  I feel the need to remove everything that may have been wet or dampened by water coming in through the tiles.  Naturally, the gutters, facia, soffets will also be replaced as well. 

Is all of this work overkill?  I'm afraid of mold and mildew. 

I'd also like to take out the ceilings in every room of the home. ( They're nasty popcorn ceilings anyway) and do some additional home improvements. 

Do you think I can/shold hire a GC to get all of this accomplished (time and money are primary concerns) or just sub-out each task separately? 

What condition is the existing tile in?  We have remove tile, stacked the salvageable tile, replaced the decking, installed Tamko, Metal and Tile, high temp underlayment and re-installed the roof tiles.  We had to re-order additional tile, but used them on the rear of the house where they weren't noticeable.  We've also taken tile/slate off porch roofs, installed standing seam copper and used them for repairs where obtaining exact matches we not possible. 

I don't understand why all the tile have to be replaced.  There are businesses that specialize in re-claimed hard surface roofing.  Look for another estimate from another roofing company. 

Just to look at the tiles, they don't appear to be cracked or anything.  The roof was sealed and painted, about 5 years ago, so there has been ongoing maintenance.  I'm not sure why all the problems on my side of the roof, when the adjacent duplex says he is having none. 

Just to look at the tiles, they don't appear to be cracked or anything.  The roof was sealed and painted, about 5 years ago, so there has been ongoing maintenance.  I'm not sure why all the problems on my side of the roof, when the adjacent duplex says he is having none. 

Could be he wants you to fix his for free...just a thought. 

On hard surface roof applications its important to have a secondary moisture barrier under the roofing surface.  Some installers use double felt, some use 90# roll roofing, we only use Tamko, Metal and Tile peel and stick underlayment to withstand the heat transfer from tile and slate products.  We have installed many and have never had a leak call back. 

Yes it is possible to stop at the dividing line of the neighbors unit, depending on the type of tile, fastener used and the installer doing the work. 

Love to, but a 12 hr drive to work makes for a long work day and I'm old enough to know I'm probably gonna sleep in my own bed each nite. 

Plenty of good roofers out there that can take care of your issues.  Go to the local roofing supply house, tell them your problems and ask for a recommendation of a good, established, local roofing contractor.  DO NOT ask at the big box stores for a roofing contractor referral. 

I was just kidding, Oldog.  And I'm old enough that I feel the same way.  No problems.  I am in the process of getting a few quotes from local contractors. 

Hey can anyone advise on what kind of contractor would remove and reinstall insulation in the attic, where the roof has leaked?  Would a drywall contractor working on ceiling repairs do that, or would it be better to reach out to a contractor specialized in insulation? 

I was just kidding, Oldog.  And I'm old enough that I feel the same way.  No problems.  I am in the process of getting a few quotes from local contractors. 

Hey can anyone advise on what kind of contractor would remove and reinstall insulation in the attic, where the roof has leaked?  Would a drywall contractor working on ceiling repairs do that, or would it be better to reach out to a contractor specialized in insulation? 

Dang and I was about to ask Mrs. Oldog if I could go to FL for a couple weeks...you snooze you looze