My name is Maria and my husband and I are looking to invest in a condo rental property on the west coast of Florida.

What’s everyone thoughts on this ? 

This all comes down to how you're structured, how the flip cost were accounted for, if there is a partner (you mentioned "we").If it is an S Corporation and you "distribute" or "sell" the property to yourself, if there is any loss on value, which probably there isn't, know it most likely won't be deductible if it's a related party transaction.  

I'm curious how many hosts update their listings depending on the season.

I made and mailed all my yellow letters by hand to cut and save on costs.

Savan cool well it is good to start and when it is the first deal it is wiser to be cautious and not over extend one self on the payment and rehab costs.

That is what I did here when I started investing in 2020.Here is an article with more information on what a house hack is www.rocketmortgage.com/learn/house-hacking

Any tips on how to identify markets for long term rental income?

The only reason to get your license in your context would be to get access to view vacant investment properties for yourself on your own schedule and for access to the MLS.

It is also a higher quality contact because you can confirm if you're actually reaching the owner.Mailers take up less of your time (aside from ordering and distributing), cost more, and are more challenging to track.I'd start with calling then add on mailers.Best times may vary but we find that we get the most people on the phone 8am-noon and 3-7pm.