My '93 had the same crack and was repaired about 10 years ago. It wasn't as big as yours, but i presume the repair would be the same. It was gouged with a dremel as deep as the crack went, which was about 1/4 inch in my case, and filled with resin. No issues at all since. The hull isn't cored, so there shouldn't be any hidden, more serious damage, but now you have a bargaining point.
Overall, I believe the boat is outfitted with quality parts that seem over-sized to me. This is what sold me on it over the Mac 26. The local dealer showed me how the mac hull was slightly deformed when sitting on the trailer, but the 23.5 wasn't. I'm sure it's a non issue, but it was dramatic at the time. The trailer is what it is.
Mine has a single axle and no brakes. It isn't an issue on the flat roads here, but if i lived in a mountainous area, i would definitely add brakes.
Just curious, what is the asking price? I still have mine and it is going to be sold soon and wondering what they're fetching. Some of the asking prices I see online seem a little high to me.