Please critique this plan for Florida short term rental

[Jim Stanley]

My wife, daughter, and I live in a suburb south of Denver, CO. We have a SFR residence and a SFR rental just down the street that I self-manage.

My wife is from Ecuador and hates the dry climate in Colorado also the cold winters.  She would much rather live in Florida.  I hate Florida, and more importantly, I have a REALLY  good job in Colorado and would likely take a big pay cut anywhere else.

My wife suggested we buy a Short Term Rental property somewhere in Florida.  She could go there in the winter/spring and our daughter and I could visit occasionally.  When my wife isn't there, we would rent it out through AirBNB or similar.  We would obviously need to employ a property manger.  We would be looking to at least break even on cash flow, but with property management fees and not renting it out 2-3 months per year, I'm not sure.

I bought our SFR rental with 20% down using post-tax money from selling our previous residence. I don't have enough post-tax cash for a down payment on another property but I do have pre-tax IRA money. I think it's possible to use that, but I have not educated myself on the pros and cons.

Is this feasible?  Suggested locations?  My wife is thinking Destin, but we really don't know (we go to Cocoa Beach a lot, but the prices there have really gone up lately).  Any major pitfalls to avoid? Any other comments suggestions appreciated!
Thanks!