Figuring you are looking for larger than your Chrysler for people space, otherwise why not stick with it:
S2 7.9 centerboarder..
Can't believe I am saying this... Mac 26 (good luck finding one in your price range)
Oday 26 Centerboard (lot of boat for the money, shallow draft).
Compac 23 (very nice boat, again, hard to find in that price range)...
Precision 23 (price again - but feels big compared to your 22).
Catalina 25 (swing keel)... Found all day long, and a lot of boat for the money, and sail well, easy to find parts.
Capri 26 (this is a beast of a boat to trailer, and draws 2.5', and would be very large to tow also hard to find in your price range with a trailer, but I just love the look, not sure why)
But I have to ask... Do you have a slip, or a dry slip (storage where you can leave it on the trailer rigged)?
If you are "trailer sailing" you'll find the Chrysler 22, will take you between 45 minutes to 2 hours to rig/derig (you'll get faster and get towards the bottom of those numbers with practice) if you don't (but this much work to sail wears on people fast)... If you go for a 10-12 hour day it'll be worth it (you'll likely be exhausted by the end of the day).
By the way, the larger boats, are about the same time to rig... launching sometimes can get tricky, especially with the wing-keel types, but it doesn't take longer (usually).
Also you'll find that larger trailerables (even non-trailerables), don't give you more cockpit, actually the contrary sometimes the cockpit gets smaller. The largest cockpits are in your racing boats (to make legroom for more crew). These also seem to be the ones with the most bare space below (and rarely have swing keels or enclosed heads).
I bet you'll find that you can get 3 comfortably in the cockpit of your 22, and one can "wander" above deck, or below. When you hit 4 in the cockpit it gets "confining," but doable.
If you go with the same sized boat, but want more cockpit (if you find people stay above deck more, not below)... you can get a Capri 22... it has 8'+ cockpit seats, and a nice division between skipper and crew with the traveler. However your requirement for an enclosed head isn't met. In fact using the head is tough, as it's smack dab in the middle of the V-Berth (without the hatch open a 6' tall person has a hard time). It's curtain enclosed only, boat draws 2.5' too in Wing keel model (but sails great, and they can be had for well within your range)... Consider a newer Catalina 22 Sport too.
The boat you can likely get all your hot buttons and easy to find, and in your price range is the Catalina 25. They also have a decent association Catalina - Capri - 25s International Association
. It's probably the 2nd most common boat at our marina, most are 20-30 years old.
But, my best suggestion is... see how many go with you with that Chrysler. I always liked the lines of the Chrysler 22, even as a kid. Seems like a hearty boat, and you may become quite attached to it. You might find that after a while, less people go with you (depending on how much learning you do with the whole family aboard :0 ).... and the Chrysler is a perfect fit.