iPod Touch 8GB (sure, there's a 16GB available too, but the 8GB keeps it under $250.00). This one also opens up opportunities for other people to just give the recipient iTunes Store gift cards (i.e., uncle Larry needs something at the last minute and he's standing in Safeway).
MacBook Air -- I love this thing and it's perfect for the Mac person in your life, especially if they do a bunch of traveling. Yup, it's expensive.
MacBook White -- spec'd the same as the Air, but under $1,000.00; not as sexy and cool, but still a nice gift.
Logitech QuickCam Pro -- small enough to take with you, good quality video. The video conferencing is free through AIM or Google or Skype -- what are you waiting for?
SmartParts Digital Picture Frame -- might as well put all those photos on display, right? This one doesn't have wireless, but it comes in right around $100.00, which you'll probably save in photo printing at Costco over the next year, right?
Shure SE110 Sound Isolating Headphones -- Shure designs in-ear monitors for musicians, so they know what they're doing. These headphones are awesome, great to travel with, and you'll be amazed how low you can keep the volume.