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Well, I owned...rather, still own, a Virtual Boy and it was awful. Actually, it was awesome at first because OMG 3D but it was uncomfortable to play, there were no games and I saw red lines all over the place for about 4 hours after playing it.

But if I were to say conventional systems I'd say the original DS. Why? Because I shelled out $200 for it and then a year and a half later a way better and smaller one came out, which also happened to correspond to the best games on the system. Damn you Nintendo!