Brian, that's awesome to hear! It's good to know someone has done it! I'm dry sailing out of Pultneyville, so luckily I don't have to raise/lower the mast all the time. I've figured out the trailer a little bit better.
I'm doing EXACTLY what you're talking about Brian, I leave the front winch cable out just a little bit. It will move a little bit back and forth, but it's on the bunks solidly, and it only moves about 20 feet in and out of the water.
I just need to get a new winch, so I don't have to worry about the cable breaking while winching the boat up.
Anyway, last weekend was our first proper overnight on the boat. We sailed about 26 miles round trip, to Sodus Bay, and stayed overnight at a little restaurant called Skipper's landing. Then in the morning got some breakfast at sodus point. The boat handled really well in ~10 mph wind. I'm sure I'll have no trouble sailing it up to the 1000 islands, but I may take the coastline to be safe. I'm surprised at how quick she motors under the Nissan outboard power, I was getting around 6.5 knots. I never got anymore than about 4 knots in my old Irwin 10.4 with a diesel engine. All in all not bad for the first time ever taking the boat out for a sail!
A photo of my Fiance and the 23 at the dock. We didn't really plan on making it all the way to Sodus bay, so we didn't bring the proper blanket, and we FROZE when it got down to 40 degrees. Luckily we had the dog to keep us warm