We're reaching out to other professionals who have done some investing in Alabama or who are very familiar with the market, (i.e. which are the more favorable counties in which to invest?) 

There is definitely more options for investing opportunities on the open market than on the land bank. 

If you're priced out of your current market, I would definitely look into other markets where you can find great macroeconomics, positive cash flow, and amazing appreciation potential.

While this would improve the cashflow and cap rate for resale, I'm wondering if it would shrink my market of buyers, since they could no longer use conventional financing as it would no longer conform to a 2-4 unit building.

Anyone have any thoughts on Alabama as a potential market? 

We are seeking guidance on a few key things about the market. 1) We've done a lot of research on the area and have been scouring MLS having trouble finding opportunities that will cash flow (the golden question, we know).

@Reitta Seidel, yes.Maybe sharing some of your thoughts that made you post this question will yield more valuable feedback.In my market, single family homes sell all year round.  

After the fix I want to put it on the market so I can pursue other real estate opportunities.

What have been your hurdles, if any, getting into the short term rental market? 

If you want to be more on the knowledge/digital side of skill, marketing is a good place to start.