Trailerable boat vs. Catalina 30
Buy the Catalina 30. It''s a great boat.
Setting up the rigging on a trailer boat can be a hassle unless there is no alternative to the trailer.
Rig the C 30 with a autopilot and in lighter air you will be able to single hand it from the start.
Get yourself some leather and rubber gloves. They make all of us a lot "tougher".
Good luck. You have a plan. I like that.