This property was previously under contract by a house hacker.Unfortunately, his financing fell through.But fortunately for me, I now have full appraisal and inspection reports from his due diligence.The interior has been renovated already (not great, but serviceable because the house is over 100 years old), but the exterior needs about $30,000, to include a new roof, exterior shingle repair, deck repair, separate garage work, brick work, and chimney repair.

If you're talking about a couple of missing shingles, that's nothing.

Roof had shingles missing and I noticed other deferred maintenance, one of the recent reviews was saying that the climate controlled units were having an AC issue, etc.With this being a corporation or franchise, how would you go about trying to see if they'd sell?

Who should be going first,  the sider or roofer for the area where the shingles and siding butt up against each other on the second-floor roof landing.

If your roof has 5 years or more life on it, get a new 4-point and wind mit - but please keep in mind that shingled roofs generally last 15 years on average if Florida (sun is a killer!).

Based on that, it takes about 10 seconds to see that everything but the "shingles/labor" seems pretty much in line with what I'd expect.Now, as for the "shingles/labor," for a 14 square roof, you're probably looking at $1600-1800 in roofing materials, $600-800 in demo/disposal, $1000-1500 to install new roof, and $1000-1500 to install the new trusses. 

Underneath the siding is the house .You could have different things under the siding , My old house had asbestos shingles under the siding, under the asbestos siding was wood dutch lap siding . no big deal

The guy that put the shingles on the roof, for example, would know how solid the roof actually is.

I paid $11,000 which included tear off and new shingles, new soffit and facia.

the shingles will be so cold they will break when you hit them with a nail gun .