The first sailboat for our family of 4 was an O'Day daysailor. it was 16'9'' OA, had a6' beam, and displaced 575#, if memory serves (that was 40 yrs. ago!) Our sailing venue was the Mystic River and Fishers Island Sound (eastern end of Long Island Sound). We had a lot of fun, but it got dicey at times. We added an inflatable masthead flotation device in case of a capsize.
Our next boat was an 18' catboat. It had a beam of 8' and a displacement of 2500#. It seemed like the Queen Mary by comparison. Never worried about a capsize, even when we got caught once in 30 kts sustained, with no reef! We've moved well beyond the catboat in length and displacement, but the catboat was a sailing benchmark for our family.
It looks like you are not ready for an 18' boat yet, but the 14' boat is rather small if ever you expect to go into LI Sound. If you are interested in the catboat concept, you might try to hold out for something in the 15' category. You will appreciate the added weight and beam. This will put you in the same weight category as our old Daysailor, but you'll have more beam and-therefore--more form stability. You are still in a small boat for the Sound, but you'll be better off than in the 14 footers you mentioned.
BTW, I seem to recall that all boat under 25' are required to have flotation, so that should not be an issue unless you pick up an antique somewhere.
Good luck with your deliberations!