Sailing clubs often have some rental boats. This would give the chance to try different boats to see what you like. And the chance to travel and do some sailing in a variety of locations.
ASA certification will get you trained in the basics of sailing and boating safety, And qualify you to rent those club boats.
There so many trailer sailboats in the 20' to 27' range to chose from. In the seventies and early eighties boats were generally pretty stoutly built. Then from the nineties forward production boats generally got lighter and more cheaply rigged.
A friend has an Oday Mariner 20. Nice shallow draft centerboard boat with cuddly cabin and large cockpit.
It's easy to rig, fun to sail in sheltered waters, can tow with most mid sized cars.
Weighs around 1,500 lbs.
I've been looking at trailer sailers for a while to use here in the often shallow waters in the southeast. I wanted a bit more cabin space for possible overnighting. Also wanted a bit more open water Capability.
I ended up finding Morgan 22. It's a compromise design with a shallow ballasted mini keel with center board in the mini keel. About 2' draft board up. And a bit wider hull than the Oday. At 2,500 lbs still trailers easly with a mid sized truck. Not too bad to rig. More cabin space with veeberth, quarter berth, and dinette for two.
Still has a good sized cockpit.
For more comfort and performance a 25/27' fixed keel boat would be best. Still trailerable from deep ramps, take 2 or three people to rig. Weigh around 5,000 lbs
Will stand tall on the trailer. Tow with mid sized to full sized truck.
Think Catalina 25', J24 , vega 27 etc.
My 25' full keeled older wooden boat was very capible in open waters of Hawaii where I sailed inter island often. But with 4.5' draft was a bear on a trailer.
The more exposure you can get to different boats will help in finding the best fit for your needs.
So much fun ahead.
Cheers Richard