C&C 1/2 Tonner
Gorman Express 30
That's quite a growing and diverse list. The difference between a Hobie 33 or Olson 30 and Olson 911 is huge, as is the difference between the J-29 and J-30. You kind of have two lists here. Honestly, I'd start to eliminate the less cruise friendly boats unless you plan on doing some racing as well. The S2 9.1 and Olson 911 both perform well, will cruise nicely,
but cost more up front.. much more. The J-30 is slower, and finding one that's in good shape will take some patience, but might be a good choice if you like boat work. The Hobie, Olson, and Express 27 are ULDB boats, and are very different creatures than the rest of your list. There are a lot of J-29's on Puget Sound doing a whole lot of nothing, and a good one should go for 17-19k and perform better than the old C&C half tonner. For myself, in the ULDB's, I like the Express and the Olson. I'd rather own the Express as it'll be cheaper to run with smaller sails, and I"m . Of the more cruisey boats you've mentioned, I like the 911 and would look for a Pacific Boatworks version (the 's' rather than the 'se' ). In the end though, it might be more a matter of finding a good deal on a good example of one of the boats you like. Just don't be surprised when you realize the Olson 30 can be quite a handful!
Correct on the J-29/J-30. Same hull, less freeboard. The J-29 is faster. In the PNW, the masthead version would be prefered. There's a immaculate J-30 at Shilshole that'd be on my list even though I'm not really a J-30 fan. Looks like it came out of the showroom last week. J also made a J-28c, which is a nice little boat, but like the J-35c, is very expensive.