Best:
Panasonic TZ-10. Use it all the time to take pictures of my 7 month old son. Priceless.
Worst:
Rock Laptop (
http://www.rockdirect.com/). It was meant to be a desktop replacement in a laptop but kept on overheating and crashing. After that I got a Mac and never looked back.
Canon DSLR and all the lenses and accessories. Used it for a few projects but was too bulky to use on a daily basis and ended up sitting in a wardrobe forgotten and gathering dust. Must have spent around £5k on all the bits and pieces (100-400L lens, 24-105L lens, 14mm Sigma prime, 90mm Tamron Macro, 50mm 1.8 prime, 550EX flash, 20D body, cable release, angle view finder, extra batteries, CF cards, ibm microdrives, loewpro backpack and shoulder bag, manfrotto tripod).