Yeah, I think I'd like to see Dean go to hell, partially because being saved from death 3 times seems a little too easy and repetitive, and I think that Sam would do very scary things to get Dean out and I'd like to see that. But I think that the show isn't likely to go there either, it's too far from the mainstream. But I'm hoping Kripke will surprise me with something.

Still, I'd also like to think that if Dean goes to hell, he would fit from the inside as well -- if Dean drops his act of not caring, and is fighting for himself again by the end of the season, he could still be in Hell but have something to do. They wouldn't necessarily have to be seperated more than a couple of episodes, or less even.