Don't get hung up on specific models
Here's a second to Tim's post:
Don't get to hung up on specific models for your first boat. Check the local Craig's list. You will want something that is ready to sail. Decent sails, rigging, trailer, etc. You do not want to by a boat as a beginner and immediately need to work on it or spend lots of money.
There are so many trade-offs to consider in buying a boat like what you're looking for and your list proves it. And I'm sure the list isn't all-inclusive, either.
Having said that, if you come across an O'Day Daysailer like what Sunbird22358 mentioned, I think that would be a good comparison boat. It looks like the one in his post with the red/white/and blue spinnaker. It is quite stable, fractional rigged (easier to tack), has a centerboard for easy beaching, a cuddy to keep the picnic lunch dry or as a place to stow clothing when going to weather, and is a lot of boat that, due to it's age, won't break the bank.
I don't know how much room there is but one might be able to do an overnight on it using a sleeping bag on each side of the centerboard and a boom tent. How's that for a possible pocket cruiser? And sailing with two people on board is not a crowd.
The Falcon 16 is slightly shorter but very similar and has a cuddy. Not as many around.
Since you're talking trailer and sailing on Long Island Sound, consider that a steel trailer, if it is dunked in salt water, tends to rust and they aren't that cheap. A galvanized trailer can still rust and will last longer but costs more. Launching with a crane costs but will help protect the trailer. If the boat is left in the water then it needs bottom paint.