Welcome DJPAT... you're getting great advice from experienced boaters. Most of us have put together a "must have" list based on how we'd use a trawler, and we have adjusted from there. You're near Tampa, so here's a site/company that rents trawlers and I'm sure they'd be helpful:
Yacht rental in Southwest Florida.
Also, I'd recommend going through a Captain's course - SeaSchool teaches in your area.
Frm-Home page
Good luck, and please post pics as you narrow your seach.