It really is a shame that the Dreamcast didn't do better. If it had come out one year later, and Sonic Team spent that year intensively studying how to make a good 3D Sonic game, it probably would have been the 360 of last gen. I never had one, but I always wanted one just for the VMUs. But by next gen, color touch screens built into controllers and terabyte hard drives built into consoles will replace them. Still, nothing will be as cool as using miniature Game Boys as memory cards, no matter how prohibitively expensive they were.
That may be why Nintendo's not supporting Wii-DS connectivity very much -- once the standard controllers have screens, console to handheld connectivity will be mostly obsoleted. Guess that's mostly a good thing, since it means you won't have to buy any special equipment to play Four Swords 3, or if someone finally decides to follow up on Nintendo's claim with the Gamecube that you could make a football game that lets you pick your plays without your opponent seeing them, you'll still have analog sticks on all the controllers.