@Alan Ford I think the Smoky Mtn region is as insulated a STR area as possible in regards to the virus and economics, I am getting ready to build as well and haven't given it a second thought. 

massive cosmetic repairs, crawl space, electrical, kitchen, doors/windows, attic venting and insulation.

I won't go that route on ceilings less than 8 feet but on taller ones no one knows the difference, and you don't have to get into asbestos worries in the compound, popcorn, or insulation above the drywall in the attic.

A lot of plaster/drywall issuesCurrently using Window A/C units - not sure worth upgradingWindows need replacing and needs more insulation in areas.Talking to my property managers the average 2 bedroom runs between $600-$750 and 1 bedroom from $575-$650.  

But we went ahead and put in over a grand of additional insulation in the attic, because of their complaint. 

Expected costs up to $2,500 to resolve these issuesWe found about 30’ of asbestos pipe insulation in the basement.

When looking at the deferred maintenance before purchasing, we had calculated a lot of the big ticket items (like insulation in attic, power washing repointing brick cracks, etc.) and we had even included things we could see like missing doors.

Being that I haven’t done anything with taxes yet, can I count items from previous years (i.e. new roof, insulation, electrical)?

You may be able to lay tile or floors or blow in insulation or paint and texture, but let them arrange things like electrical and plumbing.   

My agent and I have been discussing a scenario where we approach or submit an unsolicited offer to the builder for a lower price with the basement unfinished (Ie; insulation installed phase).