Long overdue update:I pursued the tenant through small claims court, and won, kind of. 

Today, he was showing me a property I had asked to see and he let me know he had another one coming soon that he thought would be a good fit for me.

But all good points. 

Good to know the HELOC will be canceled at closing—appreciate the clarification.

Being new to the area I have no clue where to start when it comes to finding a good builder, anyone have recommendations as I continue my research?

Seeing as STRs started long before VRBO (1995) and AirBNB (2008) or HomeAway (2004, now part of VRBO) this was considered when it was created.The "Augusta Rule" was a driving force.

Wishing you the best in your self-management journey, but remember, a good property manager can still be invaluable, especially if you’re not familiar with the legalities of property management.

I enjoyed the hard labor and comradery that I missed from my Navy days working in engineering.My question is, how do I go about getting more experience on paper without having to commit to an employer/contractor for a long-term position? 

Lots of good brokers/agents on here from down there.

To all aspiring house hackers and those aiming for a single-family primary to hold it as a long-term rental, what are your biggest frustrations likely keeping you from jumping in the game?