Thanks for the comments. Loosing a child is something that just isn't supposed to happen.
On the sailing side, I've always heard the larger the boat the easier it was to sail. I didn't notice a huge difference between the 22 and 27, but definately did between the dinghy and the Catalina 22.
A 40 ish foot boat sounds great, I'm just concerned about the docking fees. That may be changing with the way the economy is going, but the economy is a whole other thread.