I know if card X is charged, it's the cleaner at my North Carolina short term rental, for example. 

Frankly, I wouldn't feel comfortable owning a condo long term due to rising HOA costs and major assessments.

Before you start asking any questions you need to get an idea of what you qualify for in terms of financing.

If, however, that means you own more real estate in locations that you like, you get the magic of leverage + appreciation that results in a better long term return. 

Hello, long-time reader of BP, first-time poster!

Long term I think will be interesting to see.

What recommendations do you have in terms of what to take a look at/action items after 1 year? 

This is common in my area/Colorado in general especially the ski towns that still allow short term rentals. 

Tampa is not only a great STR market, but is also leading the way in Floridas real estate market with development, job growth, and net migration, which are all important fundamentals to long term growth.

I am on the opposite side of you on the Mortgage Banker side of things seeing things skyrocket in terms of applications right now with out of state buyers.