34'''' - 38'''' Coastal Cruiser - My wants vs. my needs.
I had a Mason 44 and spent many years and more dollars cherrying her out. She was a classic CCA design with oodles of S&S influence - very Hinckleyesque - just the sort of thing you are descibing sans the canoe stern. She was truly Bristol and the belle of every anchorage.
Long story short - since this is about you - we got tired of the maintenance and sold her. And we got a J32 - which is a great little cruising boat for what you want and frankly a lot more fun to sail on a sunny afternoon. But way definitely not the same thing...
As an engineer I am sure you can appreciate how much technology has advanced in the last 25 years - everything from design to materials...
Here is what it comes down to. There is no real replacement for the sheer joy a beautiful boat brings. If it is a burden to keep her, then its a bad deal. Otherwise have at it.
As far as performance. The Mason was an awesome boat once the wind got going over 10-12kts. Sucked in light air. We called her the Buick Roadmaster - strictly a cadillac ride. We had all the strings on her and found her to be very responsive to subtle changes in trim. I suspect the boats on your shortlist fall in this category.
Point being that once it starts to blow, (and 15 knots really isn''t even blowing) there is nothing like a bluewater boat. As the ads say, the sea hasn''t changed... A long narrow hull with a lot of lead is easily driven. A boat with overhangs is often tender - something Robert Perry equates to seakindly. Forget the hobby horse crap - with the kind of mass you have on these boats, the normal head sea is not going to stop your forward motion as it would on a lighter more modern boat.
But the Mason was a small big boat - and that is the problem you will have when it comes time to sell. The Benecaca''s are popular because of the extraordinary amount of interior volume, reasonable systems and equipment levels and very low levels of exterior maintenance. But make your heartbeat - i don''t think so...
The Mason and her sisters are ingeniously and expensively built to provide access to every inch of the hull so you have maximum storage.
Do be clear - especially if you opt for a Taiwanese boat from the 70s or 80s that you will replace every piece of stainless that has contact with saltwater. Do be aware that the black iron tanks are waiting to perforate. Do be aware that the teak presents its bill every season.
Personally, if you don''t mind the brightwork I don''t think you can do any better then a Shannon or Pacific Seacraft. Delight to sail - well maybe not so much but great seaboats, great boats to be on in an anchorage, great boats to spend a week on - yes by all means.
BTW there is an excellent book called The Voyagers Handbook by Beth Leonard - details what she learned going around the world on a Shannon 38.
Finally since you mentioned Perry, in the genre is the Passport 40 which has a phenomenal layout and great lines. Also a Taiwan boat