Welcome. Living on a boat is not for everyone so my suggestion to you is to buy that trawler before you sell your residence and spend time on it so you can get used to the lifestyle. Take short trips, then longer and longer trips.
If you're in Jacksonville, FL rather than some other Jacksonville, a trip up the St. Johns River to Sanford, FL is, in my opinion, a great cruise. There are small towns with marinas along the way and dozens of great anchorages.