I know this is an old post, but here is my 2 cents. I have a 23.5, one of the first, Hull #8. Although it is trailerable, doing so is a pain in the butt. And the trailer it came with was a little light, I feel. And it is wide, I was always nervous when pulling it on the highway and I only pulled it twice a year to launch and haul out seasonally.
As for sailing, it is pretty easy for the beginner. Very forgiving. I've had many great years of sailing on that little boat. I don't miss the cockpit rail seats at all, with the open cockpit it already feels like you are sitting almost in the water. And the little transom ladder is fun for 'body surfing' while under sail. And having an outboard motor makes servicing easy. Just reply if you have any other questions. Good luck!