On the flip side, if I keep the property and rent for the above values, I would be paying off the debt every month from the income, essentially making me debt free due to the payments being covered, and I keep the asset, which will start cash flowing a lot once debt is gone. 

I'd consider starting with letters then perhaps following up with a few rounds of postcards.

We're looking to start investing in Florida with a motivation of snow-birding at some point. 

One of the things we do to circumvent this problem is to start earlier. 

Good luck and congrats on getting started.

Where do I start to talk with someone about investing and what would make sense on paper for me to do this deal? 

I have a Schlage Encode lock on 1 property, using Remotelock and integrated with OwnerRez for code purposes, etc. works great for over a year.just started a new property a month ago.

Welcome to BP Richard,These forums are a great place to learn and meet people, whether you're just starting out or you're a seasoned investor.

@Don KonipolSo we have a short term loan with someone and as part of the loan they paid all the interest upfront (12 month loan), loan is maturing and they have extension options (for a fee) - they asked about the extensions and we said it was X amount for the extension and you would also start paying the monthly interest as well.They flipped out and am like what do you mean I have to pay interest ?

Keep in mind BP is a great incubator however there is a lot of Members just starting their journey so you want to make sure your aware of their experience levels.