Which reminds me that I should mention that I’m not opposed to living a not-so-luxurious lifestyle in the short run.

However what happens when the tenant vacates and now the unit has to be turned over/takes a few months to find a new tenant and during that same period of time the sewer line goes and you get hit with that $15,000 cap ex expense in addition to the vacancy and turn over costs.

You should treat it as a luxury package rather than regular STR. 

All a mid-term rental is someone staying not permanently but longer than on vacation.

Rodrigues' recommendation may change this), but my next question would be, are there any cities/markets where 1 of the following are true: 1) You have family/friends that live there, 2) You travel there frequently (either for vacation, work, etc.), or 3) Somewhere else you've lived before AND know the area well?

Provided I can establish a solid investment plan tailored to their financial needs/comforts such as debt ratios and income, they would be more than happy to offer me some financial control.Additionally, If I wanted to, for the sake of building my own personal wealth, I admittedly have the luxury of taking a loan from my parents.

Our buy box specifically focuses on vacation destination accommodations - including boutique motel/hotel, campgrounds, treehouses, cabins, etc.   

Were you investing with a vacation loan / 10% down?

if you're in St Pete frequently you'll need to turn some of those vacation trips into work trips - networking, building a team, and trying to find a distressed property.but the trick is then going to be moving quickly if either 1) a distressed property hits the MLS (unusual, but not unheard of) or 2) a distressed property comes to you another way (from your network, from a wholesaler.)how you will move quickly enough to lock it down and buy it, if you're in RI? 

Hello everyone, I am analyzing the Indio, CA market as a short term rental investment and we'd love to speak to someone who is self managing their own vacation rental.