I've been trying to beautify the space, add a bathroom, flooring and paint.  

Perhaps you could offer some labor in return for the privilege of watching the process (demo, painting, landscaping, etc.).

I never paint it unless it is 1) trashed or 2) already painted.  

We have experience in everything from framing, trim, paint and even have done a good amount of custom cabinetry work, can't think of anything we haven't done.

Condition of home is also good, maybe $2000 for new windows and fresh paint. 

I've inspected all 15, and 11 had tenants that have lived there 8 years or longer, 4 since the 90's. 1 is vacant ( they turn quick at that price, but I'm going to experiment with raising rent with hud when I close the deal on that one), 1 was disgusting, and 1 guy painted the house like an African jungle.

I made a contractor very upset by not accepting his bid and am trying to figure out if I broke some important etiquette rules of dealing with contractors.The story is this: I got two estimates from painting contractors for exterior painting of a large house. 

Skills needed are drywall repair, painting, and possibly some landscaping.  

2) Lead Paint.

Many contractors are used to doing full gut rehab but it's rarely worth the time, money or energy when you can create a similar looking result with some new flooring, tile, paint, fixtures, trim, or decorations.