By having it as a STR I am equipped to immediately put it on the market to sell it and it's already staged which is kind of nice and I can also choose to market it as medium term rental , someone that needs to work in the area for 3 months so i get the best of both worlds.   

I am planning on doing a lot of the rough ground work myself as I have the equipment etc.. to do so, but once I have some numbers on the things I will be hiring out, I'll gladly share if you'd like.  

You're also going to need to supply some basic cleaning products and equipment if you want people to be able to pick up after themselves - which you absolutely do!

Or do you simply assume all contractors do the same work, the same way, with identical materials?

Structural roof components shall be capable of supporting the roof-covering system and the material and equipment loads that will be encountered during installation of the system.1511.3 Roof replacement.

Many contractors also like to or need to in some cases drive onto the lawn for ease of install of appliances, use of equipment such as lifts and fork trucks. 

I am assuming the units are not all identical? 

Emergency escape and rescue openings shall open directly into a public way, or to a yard or court that opens to a public way.Exception: Storm shelters and basements used only to house mechanical equipment not exceeding a total floor Area of 200 square feet (18.58m2)R310.1.1 Operational constraints and opening control devices.Emergency escape and rescue openings all be operational from the inside of the room without the use of keys, tools or special knowledge.

Did not mention anything about it being installed improperly, that it was missing equipment, etc. 

The first year we lost a significant amount of money for equipment that was not included in depreciation, as our CPA was not familiar with it.