Re: Help me find a boat for next year
Both of these are very similar boats. They sail really well and are built very well. Yankee 30s are mostly on the west coast, I don't know where you'll be shopping. They have a huge B/D and are very stiff boats in a breeze, but move pretty well in light air. A couple of my friends have them and they are lots of fun to sail. Yankee 30 has chainplates going to fiberglass knees, which is a huge plus in my book.
There is a nice one of these with a repower that has been for sale on my dock for a long time. You could probably get it for a song at this point. Smallish interior, strongly built, no liner which is good in a lot of ways.
Huge freeboard comes with that clean spacious interior much of the time. If you are looking on the east coast I'd say that it is worth looking out for a mid-80s Pearson 31-2. I have the 28-2 and am impressed with the construction quality and how it sails. It's a bit freeboardish, but the 31-2 (which is 30.5 vs 28.5 feet) should diminish that a little bit. The cockpit on my 28-2 is ergonomic and great for singlehanding, I love the interior space, and the boat sails very nicely balanced in a variety of conditions. 28-2 has chainplates going to fiberglass knees, I haven't looked at how this is done on the 31-2. Both of these came with the Yanmar 2GM20F, which is a robust little engine.
There are lots of other great options to consider like C&C 29, 30, 32, Islander 30 and 32, Cal 31, Erickson, etc. I just wanted to mention a few that are perhaps less common.
1986 Pearson 28-2 "Elena"