This has always confused me!

Mary didn't make a deal for her soul. She made a deal with the YED that he could come into her home and drip his blood into Sam's mouth. As for part 2 of your question - John crawled out of Hell. And Mary was never in hell to begin with.

me personally i don't think John is in hell anymore after he helped Dean kill Azazel in AHBL Part 2 he flickered like what we saw in "Are You There God, it's me Dean Winchester" from Victor when he goes after Sam in the bathroom. So in the long run you have a good question i would think if either John or Mary were in hell Demon's would brag about it to the boys..but who knows i could be going the wrong way here...lol. Really good question though

Good question... *strokes invisible non-existent beard thoughtfully*

I think John is now in Heaven (after being free from Hell in 2x22)
But I'm really not sure about Mary, now you have me thinking lol... :S

mary made a deal with yellow eyes to bring back john in return he would come into sams room to drop the blood in sams mouth. when she was a ghost in the house that phsyic said her and the poltergist ghost canceled each other out so shes nether in hell or heaven. as far as john when they opened the gates of hell his soul was set free and sent to heaven.