Crossroads demons don't collect on the bargain till the agreed on time period is up, and the person dies.

The people in Crossroads lived the ten years of their bargains just fine, souls in place, but with a lien. Dean lived for a year. The soul doesn't go anywhere until the deal is up, and the person dies.

The soul doesn't go anywhere until the deal is up

But Crowley has the soul now. That's why I'm confused.

Crowley: I fully intend to give it back.
Dean: Well then give it back!
Crowley: I will.
Dean: Now!

So what does that actually mean about/for Bobby?

I'm beginning to think the Buffyverse might make more sense than this.

The implication in S3 was that the demon holding the contract could make it null and void (and in S2, we see that they could do that without undoing the granted desires). So Crowley could release the lien on the soul. My impression is that Crowley has soul rights via contract, not the physical possession, and that the writing was a little fuzzy there.

I think he has a lien on the soul. Like buying a car. Technically it's the banks until you pay it off, but you can drive it.

And Plei has my brain. Again.

I assume that if the demon who holds the deed to the crossroads deal dies, the deal is broken, ownership of the soul reverts to the person who made the bargain. Sam kept trying to find and kill the demon who held Dean's contract. If a higher-level demon offs the one who holds the contract, or simply decides to take over his or her corner, then the deal stands, but with the more powerful demon as lienholder.

triplecross post!

I assume that if the demon who holds the deed to the crossroads deal dies, the deal is broken, ownership of the soul reverts to the person who made the bargain.

Then Crowley isn't protected against death by holding the deed.

Yes, but he's King of the Crossroads. Top of his particular food chain, if he's a reliable source. I have no idea of the workings of hell's hierarchy, but I can't picture the demon in charge of flaying, who has a little seniority over Crowley, deciding he wants to move in on crossroads deals. Could happen, I suppose, but it doesn't seem likely.

And if you're talking about Crowley dying by a mortal's hand, then you're right. That's how attempts to break crossroads deals usually go, by killing the demon who holds the contract.

I assume that if the demon who holds the deed to the crossroads deal dies, the deal is broken, ownership of the soul reverts to the person who made the bargain. Sam kept trying to find and kill the demon who held Dean's contract.

Sam assumed that, but I don't think it's accurate. There's probably, like, demonic probate courts and codicils to the contract like, "Kill me, Dean Winchester, and Bobby Singer never gets the clear title to his soul."

Oh I'm sure Crowley's made sure his ass is covered. Sterling never loses, after all.