I trailer sail a Capri 22 (faster than a cat 22, and slightly more complicated to rig). I've trailer sailed it and I also slip it.
Denise is SPOT on, for cheaper than wet storage. If you have a decent tow vehicle, and want a larger trailer sailor (18-25 foot), dry storage is an "easy/cheaper" option.
My capri 22 has full height shrouds, and a single set of lowers, is fractional headstay, and split backstay adjustable. Total rig/launch time is about 1 hour. Total derig/and pull is about the same hour. That's with motor/fuel tank rudder, sails bent on, running the lines aft to the cockpit, etc.
I've even rigged it all up so I can raise the mast myself (which is astonishingly hard to do without some kind of "mast upper").
So I won't say day sailing a 22-24 footer is impossible (as I just did it 2 weeks ago)... but it really makes for a long day on the water... an overnight would make it more palatable.
I will also offer yet ANOTHER option. Trailer sail for longer weekends. You can get a "transient" slip, meaning a slip for a couple days. Then trailer launch your boat, slip the boat for a few days at a time, and pay only for those days you use! However, keep in mind if sailing is 4-6 times a month, at 2-3 days at a shot, it'd likely be cheaper to have the permanent slip.
As yet a final option, have you looked into private docks? Not knowing where you sail, I'd say most water has private residences with dockage (which are hard to vet out sometimes, Craigslist can be a friend here). Keep in mind parking and access (odd hours might offend) might curtail usage to some extent. But it also can offer great opportunity to get simple upgrades (like WIFI, or electric) for those times you really need it.
I've considered all the above. I pay the ridiculous fees for my boat for dockage. In fact in 2 years slip fees I've paid half what I've paid for my boat (it was a cheap boat)! The convenience is nice though I must admit. Having sailing dockmates is also a benny (sometimes an extra hand is good to get and to give for learning).
I like to be able to just hitch up and grab the boat though.. We'll see if the jones for larger water overcomes my inherent laziness of the quick sail.
Good luck and let us know what you wind up getting.
If you go the trailer sailor route, don't forget to check the board that lives for that stuff, not that I would send anyone other than this board for sailing stuff