OK... The "perfect" cruiser/racer (emphasis on cruiser) that performs well to windward and can still gunkhole... centerboards seem to be the answer. General comments on 40'' and under models as this boat will be singlehanded often. I am looking for a fairly simple design so that maintenance is not a huge factor (ie. no bleeding edge technologies). I am looking for a solid proven design and your comments are welcomed. Budget is from 25k-60k, pref. <40k
You might want to try posting this question on the Buying a Boat board. Based on a centerboarder and your size criteria, a Tartan 37 comes to mind. Some of them will be a bit above your price range, but there may be some around worth looking at.
Even the older ericson 35 would be a good choice. They go to wind respectably, especially if one installs new tracks further inboard. These boats are still competative and they can be single handed easily.