Engage an architect, they will be able to advise you on how all of the issues written about here do or do not apply to your specific parcel. 

It looks like checking out websites like Zillow and BiggerPockets for cash-flowing properties in Fairfax, Virginia has been a bit tricky.

For Maryland and maybe more specifically Baltimore, search @Ned Carey posts. 

That way you will get other investors working in that area to give you more specific advise.

Revenue Ruling 2002-83 is the specific ruling that covers related party transactions. 

I have been on this website for a long time and it’s embarrassing to say that I have had life/ analysis paralysis for many years now.

Perhaps more than one to accomplish specific goals. 

@Lindsey JohnsonLove to pick your brain on what worked and did not as I want to try this in a specific market.

I just can't figure out what is best for my specific situation.

The BP Brandon Turner multi family book is a good read for that... some of the content that could be useful to you is calculating your cash flow, specifically running through the various expenses an investor has and the different types of financing and the limitations of each of them.