We have zero concerns of squatter in SWFL.

If experience is your concern, you can easily partner up with another experienced investor in your area to help balance the risk out. 

But once I got the bills, I increased the rent with the tenant's approval and signed an addendum to the lease stating the rent increase would be X and the owner would take over utilities.

Top 3 reasons owners hire PMCs:1) No time to manage correctly2) No time to learn how to manage correcly: laws, documents, processes, etc.3) They're too nice and need someone to "save them from themselves"A good PMC can usually earn their fees by better managing the property/tenant than the owner, thereby:1) Increasing owners net profit2) Decreasing owner's time commitment, stress, headaches, etc.No matter what though, you should always plan to commit a couple of hours a month to manage your PMC.

All this makes for great guest reviews and helps increase revenues. 

This would increase the benefit to where the fee would not be so outrageous that it would hinder the investment.

Additionally, confirm the transfer won’t lead to property reassessment, which could increase taxes.

I understand if you want to sell 1 of the lots, but I'm not sure about your concern about paying off the debt so that you own it free and clear. 

My concern is that a lot of younger, inexperienced and unsophisticated folks get fooled into believing that their hard earned money is going to "buy" property in these kinds of arrangements (i.e. believing they are not "throwing money away on rent") whereas throwing their money away on rent + even more money should the option fail is a better description of what is actually happening. 

My main concern is the interest rates being so high now as to whether what I'm hoping to achieve is really even possible.