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.
Thanks for the suggestions.
There is one Hunter 33.5 I'm going to try to look at in New Jersey.
The Catalina 30 started making a walk through transom in 1990. The also changed the floor pan, raising the floor up a couple of inches. Believe it or not, I cannot stand up anywhere inside this model Catalina 30.
The 1989, before the walk through transom, has standing headroom because they used a different floor pan, you can actually see that it bevels down a about two inches at the edges all the way around the salon.
I just looked at a Beneteau First 310. Great boat, NO headroom. Too bad.
O'day 35 is too long for my mooring regulations. I considered the O'day 322 but it seems there are some design and quality flaws at the end of O'day's run. Not slamming them, but I'm second guessing them. Otherwise the 322 has most of the things on my list
I could not find any Newport 33's with that design for sale. I do like the layout down below on the 30. Like the O'day's, I'm concerned about build quality in the last couple of years of production.
I know I'm sounding very picky, but this is my life savings we are talking here