The third generation boats like the 31.5, 35.5 and 38.5 were excellent boats in terms of build quality, seaworthiness and sailing ability, especiallyas compared to the earlier designs (with the 31.5 being my least favorite of that series.)
I am a very big fan of the Bristol 34 which was a Halsey Herreshoff design and represented a big leap in build quality, seaworthiness and sailing ability over the earlier Bristol 32's. They are comparatively rare boats but I was aboard a nice example last year.
I have a fair amount of time on and racing against Luder 33's and on Bristol 32's for that matter. While I like the Luders 33 better than the Bristol 32, neither are especially good boats for the Chesapeake (really poor light air ability and really poor behavior in a chop) especially as compared to the Bristol 34. I think that you would be disappointed in both the Luders 33 and Bristol 32 as compared to your Bristol 29.