If you see yourself actively involved managing a company head towards self-management.

@Chris Mason Nailed it on the head.

Of course there's the risk that not fixing the foundation right away will just cause me a bigger head  ache in a few years.Thanks @Rick Pozos and @Ryan Hawkins.

Thanks for the suggestions on locations & the heads up on the scammers, Patrick. 

Keeping in mind that every month the property is held on to, he goes deeper and deeper in the hole.Holding out any longer is not investing anymore...it's speculating.If you are headed to a particular destination of great interest, in a rowboat, and about 50 yards off shore you realize the boat has a leak and is sinking...fast, you have two choices:1 - You can row faster, and bail even faster (wait, no partner in the boat, so you have to choose between those two...I suggest rowing like you've never rowed before). 

After I close on the Orlando property and get my renovation done I’ll head out to Tulum for a trip to look at options. 

I’ve lost a substantial amount of sleep over it and thought that maybe putting it on paper would help clear my head a little.

@Joshua S. it the nail on the head with "if you were staying there, what is the minimum you would you want." 

Just curious if we are heading into something.

I live 2 hours out of the city, so having my own property to book and stay in would provide a huge personal benefit in terms of being able to head into the city more without the stress or hotel fees.I guess I'm mostly hoping to hear if anyone has done this ... my initial concerns are (1) potential complexities with how the entity is set up/ business or otherwise/managing the books, (2) negative perception among vacationers in a complex or duplex format, and (3) finding a property manager that can manage some of the nuance of STR (such as cleanings) with the general maintenance of LTR.