The only inconvenience is I have to pay booking.com a commission at the end of the month, and I have to remit the local taxes myself vs.

This is the cleanest way to do it, but transferring it post-exchange could have tax or lender implications. 

you are in the right place for learning . every day read as much as you can and soak up all the invaluable knowledge here on these posts .

I doubt after factoring all of the expenses/reserves you'd be at $1100 per month in Net Cash Flow but still way ahead of the expenses nonetheless.We have a duplex bringing in $2800 per month-expenses $1253-debt- $740(P/I) and netting us $807. 

Sounds like you need to have a relationship with a couple of good contractors, 40k for vinyl siding sounds high, what was the material cost.  

Here in FL a pool trumps all and having a spa feature built in offers additional ROI. 

This approach will give you a clear picture of both rental prices and demand in your area.

I can connect you guys, if you're interested in real estate shop-talk. 

A professional home inspection can help you avoid costly surprises by uncovering potential issues before you buy, renovate, or rent out a property.Key Areas an Inspection Should Cover:✅ Roof – The home's first line of defense.

As others have alluded to, buying larger units or a house near the beach is a better play.