To me the first decision is if you want racing or just recreational sailing. If you want a little bit of both, just make sure you are not leaving doors open "just in case", it might lead you to a not so good decision.
If you want some racing, I don´t have an opinion (better listen to the experts). If you want recreational sailing, I would follow with:

- Define the size. 14, 16 and 18 feet boats are different animals. The size is not proportional to lenght (think what happens if you double the radius of a sphere). Try different boats and see the difference, the decision should be very straightforward, just compromising with the ease of rigging, righting and moving, but these things have been pretty much solved I think, you just need to figure out if the extra effort it´s worth for you or not.

- Go over the compromise of performance versus simplicity, it also defines the kind of boat you want. (decide if you want boards and boom).

- Then look at your budget and start over. A couple of iterations should be enough.

I´m sure I'm forgetting something, but just don´t overanalize things.

And make sure that your boat has room for your wife and children, "just in case"..... I frequently sail with my wife and two daughters, all on board. And they are not too crazy about sailing, but like to get a ride from time to time. Even my mother join us sometimes, like in this picture. (yes, the one on the trapeze..)