Ok, don't know if this thread is still active, but want to than everyone for their excellent advice....
I'm coming in late to this thread, but have some more advice if ya want it.
I started off sailing about 6 years ago after having fun with a Sunfish. After looking around I bought an O'Day Daysailer. Perfect boat in many ways, but for more than just my wife and I it became too small. Went up to a San Juan 21 and loved it but found that I wanted to actually spend the night on it once we got a slip (and still occasionally trailering it around.) And it was a tad bit small for my whole family of self and wife and two older teen kids. So now I'm looking at a 25-27 foot boat. And so it goes.
So my sage advice is:
1. A new sailor will feel like any boat is big enough, but a small boat rapidly and mysteriously becomes small after a year or so, especially with a growing child.
2. Sailing and managing a larger boat is not harder than a small 14' boat. In some ways it is easier because the motions are a little slower and more deliberate.
3. The stability of a larger boat with a weighted CB or keel is more stable and comfortable for a family to enjoy sailing.
4. One can buy a larger boat that is trailerable. Getting it in and out of the water may be a little more problematic than a tiny boat, but it's just a matter of planning and maybe using a mast winch system. It all can still be done singlehanded if you want.
5. After a year with a small boat you will be looking for a larger boat. Trust me on this.
6. The Flying Scot looks great. It is very stable and comfortable and yet can be raced or just wild-assed sailed solo for tons of fun.
7. Do not discount the value of really comfortable cabin space. After a day sail it is heaven to hang out with a bottle of wine, a loaf of bread, and thou, or at least some toys and books and a sippy cup.
Welcome to the club.