Considering all of your requirements, a few are going to be tough to meet. In a boat 30-33' finding one with a large head will be difficult. Finding a walk through transom will also be tough. When you put the max price at 40K you restrict yourself to boats from the mid to late 80's and early 90's. Very few boats from the 80's came with open transoms. Some, like Newport and O'day, came with swim platforms. Maybe that is good enough?
Some specific boats you should consider are:
Catalina 30 - boats in the early 90's came with open transom
Hunter 33.5 / 35.5 - as mentioned
O'day 35 - no walk through transom but it does have a nice swim platform - is that good enough?
Newport 33 - again, no open transom, but real nice swim platform with steps.
Beneteau First 310 - I don't know anything about this boat but it looks like it would fit the bill.
Day To Remember, 1986 O'day 35 For Sale
Deep Blue C, 2002 C&C 110 For Sail
Mt. Sinai, NY
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