Can an Endeavour 37'''' be a good boat?
My mother owned an Endeavour 37 which she bought in Annapolis and took back to Florida. These boats are a real mixed bag. They were nicely finished but not so well built. They had a nice interior layout and good ventilation, but really did not sail all that well. They offered a lot of features for their day, but had one of the most uncomfortably rolly motion in a seaway of almost any boat that I have sailed in my life. They were quite slow and had underwelming deck hardware. They were useless in light air (which makes them a poor choice for the Chesapeake) and I thought they were not too good in a blow either.
They are now getting up in years and should be surveyed by a really competent surveyor. Beyond the normal concerns I would especially pay attention to the rudder condition and look for delamination in the area of the encapulated keel.