Condo for us part time / renting out part time

[Kenneth LaVoie]

I posted here about how my wife and I have been agonizing over buying a condo for ourselves in Southwest Fla for years: https://www.biggerpockets.com/forums/530/topics/32...

We are close to talking ourselves out of it, mainly because we won't be able to use it that much over the next 3-4 years because our daughter is still in high school, and then we have plans to travel more and more of the world (vs hanging out in our condo) as we feel safer leaving darling daughter to her own devices. 

What would tilt it "back in the favor of buying" is if we could at least come close to breaking even by renting it out. (VRBO, etc.) Then we have the benefit of "diversifying" into another market (we own 11 buildings totaling 48 units in Central Maine right now). 

That being said, is there a simple way to find out which cities or towns (in general) allow weekly rentals? I suppose a better question is, "Where can we find a cram course in buying vacation rentals in SW Fla?"

We're strongly leaning toward Venice, Englewood, Nokomis/Osprey, Cape Coral, Bonita Springs, Sarasota. (BOLD are strongest leanings) We WERE looking at Naples / Marco Island but think it might be too built up in Naples (busy), and possible too far removed in Marco Island (???). But if we're going to pull the trigger, we need it to be what WE want (ocean front or close to it, low spring break craziness, laid back but not 45 minutes to Piggly Wiggly etc., and able to come close to break even as possible renting by the week (or even once per month if that's all that's allowed...if they put a "minimim one month" lease is it practical to literally do a 1-2 week rental once per month? do people do that??)

Thank you for any feedback.