In today's market, what innovative strategies are you using to maximize ROI on properties that might traditionally be considered high-risk or low-yield?

I'd say first, figure out what kind of investing you're into and make sure that the market you choose supports it. 

I just accepted a job as a marketing coordinator for a local RE agency franchise office, at 21yo, a recent college grad.

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.

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

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).

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.

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.