The biggest thing that is going to help you with many of them is to buy right.

Again, I think the biggest question you'll want to address for yourself first is short term or long term rental?

There is actually a condo for rent where I live which is a sought-after complex but I'm unsure if I want to invest in a condo.The biggest thing I need to work on is meeting people around here and also in the NY area who are actively doing what I want to do.

Here is my biggest concern.

Most property managers charge a percent of income collected, ensuring their incentive for collecting rent.

I believe the biggest disadvantages are purchasing at close to market rate and not being able to force appreciation. 

My biggest issue with it is the lack of required documentation.

Either way, my biggest advice is to no lose your mind overthinking it.

TLDR: Seeking advice on whether/how feasible purchasing a three-unit RT-4 to convert into owner duplex and one income unit is and still qualify for historic tax credit adaptive reuse incentives at federal and state levels, and welcoming any service provider recs to make it happen.The property under consideration: an 1880s 3-flat with a full unfinished basement. 

Since I'm not really well connected in the HR department for the oil and gas folks around here I figured that would be my biggest obstacle.