I've worked for several PM firms in the area and one company stole like 30k in commissions from me when I no longer wanted to work at their god awful company.I can definitely advise you on some property management companies to stay away from, as well as some new and upcoming property management companies in the area that are taking a more hands on and professional approach.  

My main question is would it be advisable to start by diving in and learning through hands-on experience as I go?

@Mariangela Ciciarelli I wouldn't advise having your first STR in the Orlando/Kissimmee market specialty if you plan on self managing.

My journey has introduced me to the strategies promoted by Anderson Business Advisers.

Do You know roughly how much it would cost if I were to have a lawyer represent me and possibly take it to superior court like you advised. 

They will advise you to have one in the state.

I would advise taking a year before you start.  

Can you advise on how much escalation you think is a reasonable escalation to lock in the deal?

If it "worked" there would be more success than failures, but there are FAR more failures than successes, so how can you be ok with telling people or advising people to do it when you know DARN well that every 1000 people you tell to do it, 999 will fail.

Readers are advised to seek professional advice.