Each market has its own dynamics and risks, so spreading your $5.3M across Hawaii (Kona), Miami, and Honolulu could be a solid strategy.For the short-term rentals in Kona, Hawaii, the tourism industry there is pretty robust, but do keep an eye on local regulations and potential changes in the vacation rental landscape.

I've seen some beautiful outdoor paths & patios done this way etc, fill in the gaps with sand or concrete.You might also donate it to a habitat for humanity store (call and ask if they'll take it first) where they might get it in front of the right set of eyes. they might give you a tax donation receipt?

Having this bird’s eye view of my income for the next few years, how can/should I be optimizing this situation?

(I do not live in Orlando, my retired father does)... and my father takes care of all the maintenance (repairs, hiring contractors for electrical, HVAC, roofing, etc.) as well as showing the property for leases, he is my hands and eyes there... all for free, I do not pay him a salary or any compensation, and he does not want one. 

It's the shady ones that really do not want to be seen in the public eye. 4.

Keep an eye on city plans and big projects that could change home prices.

Still have my eyes peeled!!

Keeping an eye on the local rental market will help ensure you’re charging a fair market rate.Remember, you’re doing great!

I place only used and would never pay for a new stove or refrigerator.I simply keep my eyes out for good working stoves and fridges and usually have a couple spares on hand and if something goes down that is not an easy fix I just grab the trailer and dolly and exchange it.And in my area you can find working white stoves and single fridges for $100.00 each if you pick it up yourself.

Yeah, real estate makes a lot of people's eyes glaze over.