I've been through all this.
My wife & I both learned to sail as kids
We started renting
boats. Easy, just rent and go, and return the boat.
We bought a Catalina
sailed it to a lake 3 hours away in the summer, sailed it off the trailer locally during the winter. Left it in the water
during the summers - great - felt like a big boat. Then each winter it became more and more of a PITA to sail it, even though we could leave the mast
up and drive two blocks to the ramp
Bought a Catalina
25, fin keel
, left it in the water. Owned it for 12-13 years. Great boat.
Finally bought our current
boat in 1998. Luxury.
I'm currently working with my son to replace the muffler
riser and lots of hoses.
Each of them was "perfect" boat for that particular time in our lives.
All the advice
you're getting here is valid. Only YOU can determine what will work
for you and yours.
Good luck and welcome.