.: Quote from @Chris Seveney: @Dana YobstBlows my mind how he is out there still teaching classes and going on as nothing happened but it sounds like these debts are not getting substantially paid down.As many of us know, one of the main reasons he's able to continue on is with the help of this other self proclaimed criminal https://weclosenotes.com/ep-nc-03-protecting-yourself-using-a-corporate-veil-with-aaron-young-from-laughlin-associates/ Using a remote entity to limit liability is a life blood of insuring investment into all types of job creating, life saving and life improving business development.  

Same owners, same management (self managed), both STRs.

Is self management attainable, yes...

You should either buy with a DSCR up front if the property is eligible and self fund your rehab or hard money for acquisition, do most rehab to common areas with the exception of additional walls prior to refinancing into a long term DSCR loan. 

I would probably only want to buy a condo-tel personally if I were going to self-manage it.

Real Estate Express, Kaplan, and The CE Shop offer online licensing courses with continued education, including investment and creative financing topics.

If you only look for the input you want, you won't get the feedback you need.Self-awareness and self-analysis is a crucial part of investing.

Second, are you planning to self-manage or hire a PM?

I prefer to self manage because its insanely cheaper and honestly not a huge time commitment.

Depending on how much you'll like to contribute to this retirement account keep in mind the self employment taxes you may need to pay of 15.3% and age if contributing to a traditional not roth type retirement account.I agree with the above based on your answer you most likely won't have issues in FL.