House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

I applaud Brian for personally reaching out to respond to the situation and make sure things are addressed going forward. 

I heard about bigger pockets from a friend of mine that has successfully built and rented multiple properties in our area. 

You don have to replicate in multiple states.  

The only way for you to understand the situation and evaluate your options is to ask a lot of questions.  

Would a bank even allow us to mortgage multiple buildings on a single lot without it being subdivided?

Multiple things can be true at the same time.

However, i would like a person with multiple rentals to help guide me to avoid some simple mistakes.

However, there are multiple documents that emphasize that all 1245 property determinations must be factual and supported by corroborating evidence.

Over time, we have developed systems to handle these situations as effectively as possible.