Hey, that's a great question and definitely a smart one to ask when you're diving into the details of STR (short-term rental) investments.Let me break this down from both a tax and practical standpoint based on what I’ve seen with clients in similar situations.

And it appears that the amount of work is not high enough to hire a full time person.Does anyone have some good best-practice or ideas to show how you manage the work load and staffing for similar scenarios?

I’ve seen different things out there regarding best practices. 

I would still be a customer today except for the Florida Texting Law.

After 12 months, you've met the occupancy requirement on your deed of trust, and you can convert the property to a rental property after that.There's nothing in the Fannie Mae/Freddie Mac guidelines that says you can't rent out a 2nd home when you're not occupying it, and you could rent it out as a short-term rental or long-term rental when not in use (double check the local laws regarding short-term rentals). 

At 11 worth of years of supply, a condo is practically un-sellable!?

A few things to consider as an out-of-state investor are having a reliable local team or friends who could check in on the property and understanding the local rental laws.

It seems in order of increasing profitability:LTR < MTR < STRGiven that I'm based in the Denver metro area, unless I'm occupying the property as my primary residence, STR is out the question, as Denver has cracked down on the short tern rental laws.

I realize that, if true,  this is governed by state law rather than federal statutes, and therefore there will be fifty different answers. 

Aside from the obvious dangers, I’m seeking best practices and how experienced investors  in this area handle hurricane damage?