I didn't discover all things Woot until August 2004 (actually joined in December) so I missed out on Charter Member status, but have always loved the site's self-deprecating and unassuming style. Glad you haven't changed (much) over the years.
Keep up the good work.....oh, and how about having a few more "man, that's funny" t-shirts and less of the artistic frou-frou pseudo-intellectual shirts. The frenchie's claim of Blubberland was a much welcomed move back in the right direction. We need more fat unicorns, angry animals, and citrus pirates and less fancy schmancy line drawings. My two cents. Oh, and how about a media extender-type device that can move HD content from the PC to the HDTV. Now we're talking!
Oh, and my favorite woot to date has to be the 2 packets of dessicant and 3 air pillows I received in Banjo of Consternation V. The worst was the Taz foot massager. Fortunately, the mystery speakers that accompanied it were the Bomb!