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? 

I do not know if they offer that everywhere, but they do in the Cleveland market.

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

It looks like it was listed in March for $500K and in June it dropped to $400K only to take it off market in July.

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

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

I would definitely justify charging 1.5x the market rent for the inconvenience of not being able to move into the property. 

@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.  

The market really tightened up in the last 3 years where they were better options.