Based on your assessment of the spread, if it makes sense, then jump in and make an offer but try to push the settlement date back as far as possible to give you enough time to come up with a detailed execution plan for turning the property back into market. 

There's a lot of research you could do on VRBO/AirBNB/AirDNA to compare similar properties in terms of rates and occupancy, but my experience is that Gulf Shores and Orange Beach are more popular because of the nearby amenities, nightlight, recreation, and other things to do. 

Primarily I'm looking to get into fix and flips then move into long term rentals.

Is everyone on the same page with the long-term goal?

If rates fall, you can refinance the 2nd without touching the 1st lien.I wouldn't plan for long-term financing with the Heloc as the draw period will term out at some point.

I never use the term 'rich' and honestly don't feel we are. 

We have a single-family long-term rental in Port Charlotte that we'd like to keep the current mortgage rate, but we do have some equity we'd like to have access to. 

The main differences, I find, between platforms are the fees and terms.

Just out of curiousity why would someone choose this model over a short term rental that is isolated by itself (privacy) or a hotel? 

Income is $600,000 per year and husband and wife both work full-time non real estate jobs.
Is it true that the tax benefits are greater, or realized more quickly, on purchases like furniture or televisions to itemize...