You’re going to make more money with more leverage, but only if you can handle the debt service.

I grew up in a major football town, and a close family friend rents his personal home out for $3K a weekend. 

I had some success, but I was one person working against other people who had whole teams and systems in place already. 

If you have never done it before and do not know what all it intel's than I would suggest hiring a professional to handle it. 

My county is Very concerned about “occupancy and overcrowding”, so they made an ordinance that says, “A group of not more than three (3) persons not related by blood or marriage living and cooking together as a single housekeeping unit.”

I also recommend that you do not use the property for personal use, or at least keep any personal use to a minimum, and definitely below 14 days, as personal use will dilute the benefit of the cost seg. 

Personally, I have no issues making the full monthly payments from the start, so it seems unnecessary to pay the buydown payment just to have lower payments in the first two years.Additionally, my lender said that if I refinance before the 2-year period is over, the remaining buydown payment would be applied to the principal.

Some platforms, like Airbnb or VRBO, may handle the collection and remittance for you, but it's important to verify this.Make sure to register with the Florida Department of Revenue and Pinellas County to file and pay these taxes.

It sounded like it can be easy to "pierce the vail" of an LLC for a personal injury lawyer to go after personal assets (they sue the LLC and then they sue you).

I don't think that would have been possible with short term rentals.I personally see the risk with short term rentals in a lot of the markets.