Hey there! Since I didn't get to read your post until after the finale aired, I thought it would be fun to go back and see how you did with your guesses. :-)

I think Dean will go to Hell.

Boy, you nailed that one!

But I would like it if the Trickster was on the boys side

Ooh, I would've loved it if the Trickster had something to do with the whole situation, because I'm totally convinced, after Mystery Spot, that he's tangled up in this some way.

If Dean does go to Hell then I think Sam should kill Ruby

Well, it wasn't Sam that killed her, but she's still dead!