Because Chattanooga would be a new market for me, I’m looking to connect with wholesalers in the area, as well as contractors, painters, or other people that might help with a project like this.

At the moment I'm currently in the process of looking for an owner occupied duplex relatively close to my current work place in Westmoreland county to get out of the renting world now the I'm more familiar with the area. 

In need of a good, and affordable painter around Severn/Fort Meade, MD.

You can always call individual sub-contractors (Roofers, electricians, tile workers, cabinet guys, countertop guys, painters, landscapers, HVAC techs, etc) and just ask over the phone for at least a ball park estimate of what the costs are.

@Sean TippensWay way too expensive, find another painter.

Had conversation with painter guy, they are doing full renovation.

We had another trip scheduled for 2 weeks last month, so we had our painter take care of house #4 while we were gone.

I have my plumbers, handymen, painters, HVAC etc. 

I would advise to have 3 bids for the work (if they are bidding the whole project)...or if you are getting subs to bid (ie a painter, roofer, carpenter, electritcian, plumber, handyman etc) try to get 2-4 bids from each of those trades. 

@Brian Sanchez Did you ever find a painter?