Does it need a roof and new heating system or just paint and flooring. 

The seller is currently doing the cosmetic fixes (updating paint for cabinets, new carpet, paint). 

All new flooring, painting, throughout the house.

I provide short term rental furnishing and renovation finish list that includes paint colors, light fixtures, cabinets etc.

Ok, so I see this might have been a design flaw in the original build so there isn't much you can do unless you rip it all out.You could have it all scoped and see what's what so you can get an idea of what you are dealing with.You could comp the guests a night.

I'm a pretty handy guy but this would be outside of my realm, but my experience helps me understand how much this type of improvement should cost.Improvements: remodel kitchen and bathroom, paint interior, fix exterior scafolding.How should I go about finding a contractor?

In some homes planting the front or placing pots could increase the curb appeal, in others it could be paint or furniture etc.

I renovated the kitchen with paint and cabinets.

She promised she would have her Supervisor call me (she was so rude you think she had gotten ripped off not me).

After that, I'd paint and put a new kitchen in (likely do these myself, which I have done before).