@Trenton BrownSounds like you're staying on top of it which is good. 

Many other have warned about HOA's...stay away from any neighborhood that doesn't have an HOA and isn't zoned specifically to be STR.

They both have some more strict STR regulations than I would be comfortable with.

I did not have your advantage of working in the industry.You need to begin where you feel most comfortable, and where you think you can close a deal.

Stay on that path and you will be financially free (if you choose) within 10 - 15 years.

They will have those assets locked down so you can’t use them for about 2 years until you can get an appraisal to release them with your new equity.I would stay away from relatives funding.  

Figure out where your strengths lie and focus on that.After doing this for two decades, the biggest takeaway is to stay consistent, build relationships, and always be prepared to pivot.

If you’re not comfortable with your analysis and still want to pursue the purchase, I would recommend engaging the services of a real estate consultant holding the CRE designation and paying them for a short form report.   

I don't care what my tenants do in their personal lives and they can have an occasional guest but when the "guest" is staying there on a regular basis, they are no longer just a guest.  

Happy to share tips and help however I can—let’s stay connected!