I've never gotten more snail mail in my life (mortgage statements, bank statements, invoices, etc.) and it seems like every time we turn it to "paperless" options, the mortgage is sold and then I get all new mailed statements to turn off again.

Classic path of progress stuff in a close-ish market.The other option ( which could be very unpopular) is to sell both and preserve the down payment funds. 

I'm sure you have heard about FHA loans, they are great for house hacking, and you can get a better understanding of your next steps by hearing their recommended options as well.

well if you're interested in speaking about the furnished rental option, let me know!

If you have bad credit an FHA 3.5% down loan can be a good option.

If you want to learn more about this product option feel free to reach out. 

In FL, you may not have options on the Wind.  

This would be for an investment property not a lease with an option to buy.Would it just be through agents, if it is mentioned in the listing etc... or is there another way to find these kinds of properties?

We are exploring all options and researching what we think the next move should be.

But you always have the option of chaning it or doing it yourself.