Hi - another perspective here - I am 5' 10" and yep it can get a little cozy in the cabin. However, depending on the model year you are looking at, the builders added a second hatch on the coach roof to give more ventilation and depending on the modifications, such as adding a table etc... there is a way to work comfortably inside. My father who owned the boat before me, was 6'2" and 250 pounds - so a big guy - but he was able to sleep comfortably and function in the cabin on those rainy days with a me and my mother (though it was cramped).
On the sailing aspect, the Contessa will not be the fastest boat out there, but sailing on the Ottawa river, on a good day, Boats tend to get jammed up on the same tack due to the lack of river room and I have always noticed that I am able to point closer to the wind than many of the boats out there - that is something given my sailing skills are pretty basic.
I am taking the boat back down to Lake Ontario at Kingston, where we originally sailed her and I have always felt comfortable and safe on her even when one is caught in a storm. Like any boat, there are draw backs, but for my money a Contessa 26 is really built for solid sailing and the living arrangements can be adjusted (even with the lack of headroom) to ensure one is comfortable.
Cheers.
ivanross “Morava” #266
Ivan Ross "Morava" #266