You are better off selling via a traditional deed of trust and note.There are no benefits to a land contract in Maryland and only cons.

Traditional financing a reasonable timeframe would be in the 30-45 day timeframe. 

Traditionally we have invested in a few regional markets in the northeast that we are very familiar with, but recently we are looking to expand outside of this market.

However, in exchange for more responsibility, you also get a lot more control over your investment than in a traditional stock, where your only control is to own it or not.Real estate is a concentrated asset.

I may have jumped the gun on quitting my W2 job and starting my own handyman business as far as traditional financing goes.

I am a commercial lender but if I were you, I would look into getting a HELOC on your house from a traditional bank.  

They're not like traditional 30 year fully amortizing loans.  

Which neighborhoods should I focus on if I wanted to pursue more traditional middle class or upwardly mobile renters?

I’m currently holding a traditional IRA.

Traditional lending How did you add value to the deal?