It started with heat complaints.

If you have every lived or have family you are visiting anywhere in the Midwest, that's where I would start.  

I will make that proposal to the person I am talking and see where it goes.

Norfolk is where the majority of multifamily inventory is located, Virginia beach is zoned much more single family. 

I have been reading the online resources about getting started, searching the market, and even doing tours, but I am hesitant to jump in and buy a house as I have quite a large amount of student debt.

I do a lot of private lending and we do make some passive interest, but the good fixing flippers make the bulk of the money.

Scott as a starting reference.

You can start to educate yourself on the individual components; how much does it cost to paint on a per sqft basis or what is an average kitchen remodel.  

What do you find to be the most efficient? 

Consider starting small by house hacking a single-family home, renting out rooms, or adding an ADU if possible.