I have owned many boats, started with a 12' moved up to a 16, then a 14, a 24, and now a 20'. I will say this: I think your minimum requirement should be an 18' especially if you plan to go out in the sound. You lose SO MUCH freedom of movement and BEAM width (stability) from a 16' to an 18'. I cannot count the number of days we have been out in the sound and it went from glass calm to 2-3 foot chop, back to glass calm; this generally occurs due to tidal current direction and the wind. If its blowing 10-15 kts and is following the tide/current, it will stay very calm. The second that tide changes and the wind is blowing over top of the current, it will quickly set up a 1-2 foot or more wind chop. 16' and under boats are "safe" in most conditions on the sound, but not very comfortable, especially for youngsters and/or with a large crew on board. The difference between a 16 and an 18 is like night and day in a chop, as well as with the amount of fishing and people space you will have.

If it is feesible as far as your storage requirments and budget, I will really keep your eyes out for an 18 footer. They are small enough to handle by yourself on and off the trailer, but large enough to feel safe and comfortable in most conditions. The cost associated with going from a 16' to an 18' should be fairly negligible depending upon what type layout platform you choose to go with.