It may be worthwhile to web search for interesting boats, and where/ when possible, get aboard some possibilities at MDR, Long Beach, Newport, Dana Point, or San Diego to see how they might fit and feel to you.
The Florida boaters certificate course is online, and you could find some ABC (Power Squadron) classes near you also.
Chartering a boat of a make that interests you, with a training captain may also be a good idea, and may help you when you go to look for insurance.
Pau Hana, on this forum, and Jack Martin Associates in Solomons MD, are helpful with insurance info.
Boat Search 101, on this forum, and the make specific threads can point to owners thoughts of the positive and negative aspects of various boats.
Good luck. JohnS
Cheoy Lee 40 LRC