This is probably a long list...

Tractor w/ 42 inch snowblower attachment. Crazy money spent on this, worth every penny. I only wish I had a bigger one (preferably a John Deere, not a Sears Craftsman).

First new Hobie 16 (BRU Cat) in 1997.

Second new Hobie 16 in 2001.

Third new Hobie 16 in 2006, although this hasn't been used except for hanging Christmas lights since we had Hunter (also in 2006)...

First RV in 2001, 1978 Winnebago (you asked for risky, right?). Think Chitty-Chitty_Bang-Bang, but with no brakes.

Second RV in 2004, 1993 Tioga (MAJOR upgrade to the Winnie!).

Wedding at OceanCliff in Newport, RI in January 2005. I thought my wife was completely insane when she talked me into getting married there, but it was worth every penny and then some. Best party ever.

Merry Christmas everyone!

Mike