My biggest concern with house hacking is giving up my primary residence.

With that said, an agency agreement gives the agent incentive to work with you to find a property.

Some people seem to get locked in to one place they find, or a place a friend or family member is selling without really evaluating the available market.In a small town in East Texas I would think your biggest risk is a big player coming to town that can absolutely crush a smaller player. 

The single biggest issue in my way currently is obtaining enough cash, whether it be my own, or through partnerships or family/friend-based lending (which I am very hesitant about to begin with as this could potentially strain relationships unnecessarily when money is involved).

Finding a reliable contractor for the rehab portion and then a good property manager once it's rented seem to be the biggest issues for those who aren't local. 

The biggest issue with Stessa is that it sounded like they had very low transfer maximums(making it difficult to pay people) but it looks like they've improved a little bit on that.

I think your biggest issue with any "work-arounds" is going to be your legal liability and holding the proper insurance in case something goes wrong, which I'm going to assume you'd need to be properly licensed in order to be properly covered by insurance.

I also love your take on creating incentives for property managers.

How did you decide on this property, and what’s been your biggest learning from this project?

This is one of the biggest insulation issues second only to the attic.