I'm also in more control of who does the work and can avoid the red tape using a 203K loan. 

It's 1,000sq, asphalt shingle, not-complex.

Roofs, pool, asphalt, etc. these are what are known as special assessments and you never know when they are coming or how large they will be.

Does anybody have a good Rule of Thumb to estimate costs of hanging sheetrock, to include Tape & Float up to but not including painting?  

Lots of red tape, low down payment.

Bldg Inspector got down on his knees with a tape measure.

There is a lot of red tape and you can lose all your money with one letter from the bank.

I have dealt with mold in the past, and i would think that it would benefit you to get it squared away as soon as possible, one of my partners had a similar situation, drug his feet, and the city came and taped up the property, my partner had to put them in a hotel for 2 weeks while he mediated the mold. 

@James Jordan It'll be more bureaucracy and red tape which can be a good or bad thing depending on how you look at it.

Looking for a full roof replacement (asphalt shingles).