TakeFive has you covered... Even a Catalina 22 is a PITA to launch and rig each time. I found my Capri 14.2 a PITA to rig and launch each time (got it down to 22 minutes to launch).
So you must answer a couple questions:
Who is going to sail with you, 1, 2 or 3 people? how old will they be (a 5yo isn't crew)?
Will you be launching from a trailer each time? (this limits size based on your patience)
Will you have a mooring, or a boat slip? (this opens you up to larger keel boats to start).
What is your budget?
What non-sailor folk don't realize, is you can get a $5000 14 footer on a trailer that'll be pretty nice (newish)... or $5000 for a 30 footer that is a nearly non-functional floating (sinking?) barge... or anything in between. In between are some nice boats that will suffice with a little elbow grease, and a bit more work, but might also be a lot more forgiving to sail. A Catalina 22 which a lot like to recommend, is very much a compromise boat, in my opinion, too much of a compromise. Depending on HOW bad you need trailerable (truly easily trailerable), the Cat 22 is bested by many other boats including the Hunter 23, Capri22, San Juan 24, and a plethora of other boats.
Also , the tow vehicle is a limit to size of the boat one can trailer, but ONLY to a point. Once you get past a 1500sized pickup, you run into harder challenges trailering, such as raising the mast, and getting the boat into deep enough water to launch (there are exceptions, such as the Trip 33, and Hobie 33, that are HUGE boats that trailer easily, as is the Seaward 26rk)...
So lets start with answers to my above questions and we'll whittle down what might work best for you.
DON'T underestimate the power of getting a Laser, or Zuma (I hate the sunfish as a starter boat, we can discuss that another time), if its JUST you that's going to try this. These 14 foot board boats have a lot of fun packed into a STUPID easy to sail package. I'd argue the Zuma, or Holder 12 are boats that are packed with fun, easy to launch and are reasonably cheap used you can buy 2 for 2 people to learn at the same time. But they teach you to swim too, and a lot of people hate learning by getting wet.. which means you likely are looking for a decent sized trailerable (minimum) keelboat....
So fire away, we'll do our best.