Actually I think the Prindle 16 would be a good boat for you (as well as nacra 5.0 /nacra 500 and Hobie 16). Experience is that family and friends will want to go onto the boat together ones or so and then you'll end up signlehanding or sailing with one other that has gotten the bug after the first test sail.

I wouldn't buy a large 18 or 19 foot boat just to be able to take all out at one. Mostly this doesn't happen anyway and if it does only ones. Get a good boat for singlehanding and doublehanded sailing without overpowering you in weight and sailarea.

The Prindle 16 and other 16's are good in this respect. Maybe Nacra 570 and Prindle 18 but there I would draw the line.

Wouter