I would start with a house hack for sure.

If it is not in the scope the contractor will provide a quotation for the work and is not allowed to start the work until you approve the change order in writing with the defined and agreed upon price and terms. 

A high yield savings is a good start. 

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.