Boat 3 was a Bayfield 36. Had it for 4 years. Also have owned a Pearson 22, a Cape Dory 28, a Little Harbor 52, and now a Morris 38. Yea, cannot make up my mind
I agree that a Bayfield is not a fast boat, but as we say in my neighborhood, it's wicked stable and comfortable. We could balance this boat and lock down the wheel and it would hold its heading for an hour. It's big for its size in terms of living arrangements, although the nav station was in a weird place (forward adjacent the head). It had both the jib and staysail on a roller. Nice when the wind piped up. We like the way they look, some people don't but that's a matter of taste.
Would I consider this boat for the Chesapeake? Depends what I wanted to do.
If I wanted to do the beer can races Wednesday night, probably not. If I wanted to beat my buddies short tacking up a narrow bay, probably not. If I was into comfort, liked the look, happy a bit more off the wind, wanted a boat that would tend itself under sail without an autopilot...then sure.
We believe in different boats for different folks at different times in their lives. This time, yea, I really think we're on the last one. Yup, this time I really mean it