[SHNOOL]

The Capri 22 is a better sailing boat than either of the above mentioned, it does come in a wing keel variety, so suffers from your same drawbacks as the seaward 23... but the sailing characteristics are superior to either of the above. Also the cockpit for the Capri 22 is huge... the space below is tighter than the Cat 22, but the berths are large...

Also consider a Precision 23, its a shoal/centerboard configuration. Lots of room below, probably more space than the Cat 22, or Capri 22, but about the same as the Seaward 23.

Oday 23, or Oday 222. Starwind 223 are some others that come to mind.

If you want deluxe durable, and classy, consider the Compac Yachts 23. kind of a cruiser/heavy slow boat though.

 

[SHNOOL]

Ok, if the Oday 25 is even a consideration then my own boat an S2 7.9 would be better than everything else mentioned.
It's heavy built.
It draws only 18" of water (super easy to launch)
it's self righting with the centerboard up (yes provable)
it draws a whopping 5' centerboard down, so it goes upwind like mad
the cockpit is HUGE
comes in inboard, and outboard versions
has lots of room below, with a large V berth
5'8" headroom below
a proper space for a head.

Downside, it weighs in 4700lbs boat/sails/rigging and motor. Add about 1000 for trailer and maybe another 500ish for gear? 6200lbs? all up?

Trailers nicely though (nice and low on the road).

I would not want to rig/derig the boat even for long weekends though, but then most of these others I'd put in that category too.

The S2 7.9 is also probably the most robustly built of the list so far mentioned, and frankly the best sailing, and fastest.
Although if the 7.9 is too big, consider the 6.9 (everything good about the 7.9 in a smaller package, except it isn't self righting board up).

 

[SHNOOL]

Not really. I rent a Capri wing keel and its a tad slower than my Mark1 swing keel. I like the Capri but at least in wind keel version its not faster. There isn't a big difference but its slower upwind and - downwind I can actually retract my keel. I do like the bigger cockpit in the Capri but I like my dinette table and seats in my Mark 1.

Having owned the wing Keel model Capri, and raced against several Cat 22s... I can honestly say the Cat 22 should not be in the same time zone as the Cat 22.
Best Portsmouth rating Cat 22 is 94.7...
Worst Portsmouth rating for a Capri 22 is 90.8
96 versus 90.1 for Force 5 winds, so that answers as the winds are up question. I know there are a LOT of Cat 22 owners out there, and I NEVER said it was a bad boat, but I'll swear all day the Capri 22 is a better sailor. If you have to buy the Cat 22, the fixed fin keel model is the one to own though. Same with the Capri 22 for that matter.

So either a lot of handicapped averages are wrong, or your analogy isn't a real scientific one.

 

[SHNOOL]

Just to disagree with myself... just raced our 3rd in the series...
I got beat (my S2 7.9) by a Catalina 22! and a Catalina 25! Of course this was all on corrected time. They were all pretty far behind in real time.
Actually there is a pretty good reason for it the way the finishes were, but I won't go into it.

I was just happy to keep the other (2) S2 7.9s behind me for the race (and a J24)... I was chomping at the heels of a B25 though (well sailed with brandy new North 3Di sails too)!

 

[SHNOOL]

I reread most of the advice of this thread, and I figure if the OP follows it...
they'll own a 3500 dually diesel.
Tow the boat out to the hudson
The boat will be a Catalina 22 swing keel
the boat will sit below the waterline due to all the equipment aboard, including a Dry suit
Then will enter all the local races and expect to win with the Cat 22!

My personal opinion is the OP is more qualified to know what they want/need than we are... that includes myself.

Just go sailing, and have fun! Start on inland waters and work your way up