As I wrote on Sailboatowners.com, I had a Catalina 22 in 2003-2004.
The first year I trailer sailed it - trailering, rigging, launching, sailing, recovering, unrigging, and trailering home. To be honest, that was a real pain in the you know what, and took a lot of the fun out of sailing. It took about 1 hour from the time we arrived at the marina until the boat was ready to motor away from the dock. And it took another hour from the time we arrived at the dock until we were leaving the marine.
It is possible to trailer sail a 22' boat, but I don't want to do it. The next year I got a mooring ($110 / year from the town for the permit) and that was MUCH better. Then it took me 5 minutes to row to the boat and another 5 minutes to get underway.