Jim,
I'm betting that boat you have now has a very nice, long waterline especially as compared to your Yankee 30, and a decently deep fin
keel.
I've had lots of boats, but this old Bristol 27 is my first
monohull.
I got it for a song to see if I even liked slow boat sailing (cruising) which after 12 years or so I'm still trying to figure out.
This Bristol 27 is tough, handles squalls well, is easy to maintain, but it's 19.75' waterline and long
keel can be a problem especially trying to get to windward. In certain wave conditions, it wants to bob along.
I figured since I'd raced for 14-15 years performance wouldn't matter much, but it would be nice to have some upwind/speed performance at times.
If I knew for sure I would
cruise far and wide, I would probably get a bit larger boat with maybe 28'-30' of waterline or more.
I was parked next to a
Catalina 36 MKII in the yard recently and that boat although not on the list looked to be a pretty nice boat. Probably built in the late 1990's. Waterline length is 30.25'!
The OP is enjoying looking at these old, salty looking boats, but there are much better boats available for that kind of
money.
It's all up to the OP of course, but a new idea here and there doesn't hurt.
As far as lists go, they don't include all the best boats, but when you need some idea of what is definitely well built these boat lists by established "experts" can help.
As far as those of us
posting our opinions, sometimes people like to talk anything having to do with sailing or boats when not sailing ourselves.
For us up this way though, good sailing
weather is very nearly here.
Also, seeing that Class 40 (39.96' LWL) of Cole Brauer blasting along reminded me of the speed of a beach cat but in a
monohull. A very nice combination.
Tom