Just Traded in 92 23.5
I just traded in my 1992 23.5, which I sailed for 5 years. It had a fixed 3'5" winged keel. While the boat came with a trailer, I just kept the boat docked at my marina. From my experience, I do not see how you could keep the boat on the trailer and just launch it when you want to sail. The mast is very,very heavy, and since I had no mast raising system, it would take at least 4 people to raise and lower it. In fact the last time I lowered it I only had my son with me, we both 6 ft plus 200 pounds plus and we couldn't hold it and ended up droping it. Luckly we didn't break anything. Then you have to unstep it and re-arrange it in order to transport it. So setting it up is not a 1-2-3 job. As far as sailing upwind, I never hand any problems. I always noticed that I couldn't point as high as boats around me, but since I am not into racing, it really didn't matter to me. My boat had a roller furling jib, so I used the jib halard to raise the 'spinaker' that also came with the boat, but we didn't use it much as it was always too much work. Hope this helps.