Sylar -- I'm not sure. He already has his namesake watch, and nothing else is immediately coming to mind? Maybe a set of watchmaking tools from his shop back home? That seems kind of lame, though, since he's more or less put that life behind him. Possibly one of his mother's snow globes? IDK. Uh, suggestions are welcome?

Dean Winchester -- Again, I don't know. The Impala is already here (not that that's a small thing, anyway), and he already has Sam and his dad here, so he doesn't need a picture of them or anything. He has his pendant, his shotgun ... not sure what else the guy could get. Also open to suggestions here.