I'm curious about how this works with very differing levels of income. My first thought was that that'd break it, since the system ceases to be fair if the absolute upper limit that I can afford to bid on anything is $50 whereas my roommate can easily blow $150 on something in the category of "I don't mind too much, though I do have other things to do now". On the other hand, that would also cause me to very quickly obtain lots of extra money that I couldn't have had otherwise, so that's definitely a bonus. But it still seems like the balance of power would be quite strongly tilted in favor of the wealthier person.
As the poorer person, all the money you get from yootling should go into a budget account which you use only for yootling. That way you are guaranteed both that you won't pay more than you can afford, and that in the long run you will win as much as you lose yootle auctions.
After moving in with my new roomies (Danny and Bethany of Beeminder), I discovered they have a fair and useful way of auctioning off joint decisions. It helps you figure out how much you value certain chores or activities, and it guarantees that these decisions are worked out in a fair way. They call it "yootling", and wrote more about it here.
A quick example (Note: this only works if all participants are of the types of people who consider this sort of thing a Good Idea, and not A Grotesque Parody of Caring or whatnot):
Use Case: Who Picks up the Kids from Grandma's?
D and B are both busy working, but it's time to pick up the kids from their grandparents house. They decide to yootle for it.
B bids $100 (In a regular Normal Person exchange, this would be like saying "I'm elbows deep in code right now, and don't want to break flow. I'd really rather continue working right now, but of course I'll go if it's needed.")
D bids $15 (In a regular Normal Person exchange this would be like saying "I don't mind too much, though I do have other things to do now...")
So D "wins" the bid, and B pays him $15 to go get the kids from their grandma's.
Of course.... it would be a pain in the butt to constantly be paying each other, so instead they have a 10% chance of paying 10x the amount, and a 90% chance to pay nothing, using a random number generator.
This is made easier by the fact that we have a bot to run this, but before that they would use the high-tech solution of Holding Up Fingers.