I am eager to learn more on how to maintain my property and maximize my profits.  

These are not assets for a street level investor nor would any street level investor qualify for the management requirements let along the capital requirements with some of the smallest pools being north of $30 Million.In certain HUD sales, like those pools with NSO loans (Neighborhood Stabilization Outcome) management/administration has a duty to treat loans in the prescribed manner and must maintain reporting post sale for a year or two.  

I will start off by saying some of the answers to the questions you've posed have to do with an individual investors model and their own risk tolerance.

While they are probably not allowed to make a recommendation, they may very well be able to answer a question posed to them about which firms seem to have the easiest time getting through the permit process because the docs are complete and right the first time.And finally, check with your contractor... they may very well have the in-house resources and/or relationships in place already...Best of luck to you!

I'm sure it will help me maintain any rental properties I may acquire until it comes time to hire a property manager as well.

Not the poorest of areas, definitely not the wealthiest of areas, the large local grocery chain still maintains grocery stores there, starbucks/wal greens can be found etc.2 shopping centers, one free standing office building, 3 other mixed use properties that have restaurants, retail and office space.  

Clearly, a new build or very well maintained property would require less monthly in repairs, but these often sell at a premium. 

Great question actually....very well posed.

With a pure investor I would tend to want to do the deal differently in order to maintain access to that pool of capital.

As @Bill Gulley, mentioned we have posed a rent back situation as a resolution, but have not heard back yet.Bullet Points:2,100 Sq Ft.  4 bed/ 2 bathPurchase Price: $104,000As-Is Value: $155,000 -property appraised at $161,000 in 2014, market has gone up, but like be conservative with the numbers.ARV: $195,000 Repairs: $28,000Rent: $ 1450-1500/monthSince we are primarily Buy and Hold investors, that was the objective here.