Let's see....
we've got the "hole in the water to throw money into",
we've got the "two best days in a boat owner's life" comment.....
and a version of this one...:
Break
Out
Another
Thousand
After having owned thirty or so boats, these are usually all the comments I usually would make on this topic....
I wouldn't own a sixteen foot boat -- it's amazing how small they seem once you get them in the water.
For what you described, I would say 19' minimum.
and it's not for everyone, but don't let the haters discourage you!
Bigger really is better when it comes to boats (albeit more money)