Trailerable boat vs. Catalina 30
I have owned a couple of Catalina 22 before my curent C-30. In addition to sailing, I used the 22''s as a place to hide for a day. It''s not big enough to have a workable head, galley (hey you need coffee), air conditioning. When I bought my C-30 I had all these things so I could start spending the days and nights in comfort. And, I currently live on my boat.
Since this is your first, I would recommend renting some smaller boats for a while. But get the bigger boat when you are ready to make the commitment.