I manage my unit out of the state, but I have a semi property manager. I was exactly like you in that I thought I could handle the guests by myself remotely as long as I had a contractor and good cleaning service. We were in town to manage two guests before heading out, and I quickly realized there was 0 chance that us managing it remotely could work out. I got a property manager before I left. Best decision I made.
Three things happened that made me reconsider:
one guest asked for hotter water. It’d be ridiculous sending out a contractor for merely turning up a knob outside.
another guest couldn’t figure out the Wifi, and the problem definitely couldn’t have been fixed without me there.
the cleaner accidentally locked the second door with the key set, and I only realized it when I went to ensure the checkout cleaning went smoothly before the next guest arrived in three hours. Considering I give access to the keypad code and instruct the second door to be left open, this would’ve been disastrous.
A million such little things could arise, none of which could be managed without a person on the ground. It’s easy to think that these things can be pre-empted and fixable with enough planning and contingencies, but it’s impossible to think of every little thing that could go wrong.
The person who I got as my property manager is a long time friend who is making ends meet as an uber driver. The terms and conditions are such: I handle all online bookings and correspondence. I only ask him to handle things on the ground if anything arises with the guest, and to go to the property right after checkout to make sure inventory is okay, nothing is broken/stolen/damaged, and that the cleaning lady showed up. If the cleaning lady doesn’t show, he gets to keep the $75 cleaning fee for being a pinch hitter and making sure we’re not embarrassed by cleaning himself. This has already happened, by the way! The cleaner mis-scheduled and thought she could arrive later–it was an honest mistake, but one that would have been disastrous if he wasn’t there. For all of this and incredible peace of mind, I give him 15% of the booking (post Air fees). I also give him $20 per hr if he has to run around to buy anything or performs a service requested by me rather than a guest. I’ve already had him buy a new garden hose and laundry soap under these terms. This overall deal is significantly better than, say, the 20-40% quoted by agencies… but it’s also not a bad take for him. We’ve had 6 or 7 guests who have not had a single problem/request, and post-checkout inspection hasn’t taken more than an hour of his time. So, it’s a good gig and I see him as worth every penny. Win win.
I’d try to find someone in Fla who’s willing to do this under similar terms. Maybe the cleaning person’s kid? A college student? An uber driver or Amazon Prime Now delivery person? A TaskRabbit worker? All of these types of workers are used to the gig economy and are in a good position to work flexible hours required for what you need. You might be able to get away with 10% of the bookings, but 15% works for our situation.
Good luck! Get a (semi) property manager!