I took part in a 10 day road trip across several European countries, with a group of friends and acquaintances. We traveled with several cars, and were sharing the fuel costs. I took part several times with mostly the same group (we organize it every year), and this was the first time I was the driver, and used my private car. I had three others riding in my car with me. They were more like acquaintances or distant friends, not my closest friends. I had much closer friends in the whole group, but they were driving their own (full) cars.
Half a day and a few hundred km after the start my car broke down in such a way it needed several days of repairs. I left it at a service station, continued the trip with a rental car, and we picked my repaired car up on our way back. (note that my car was not in a bad shape at all, so this event was totally unexpected)
However, that rental was really expensive. We didn't have many options to choose from on a Friday afternoon, and the cars were all high-end models with large daily rates. None of us knew anyone in the vicinity to borrow a car from, so this was the only solution to continue our journey. It's important to note that the accommodations were already payed for, which was not a negligible sum either.
Near the end of the trip, one of my three passengers volunteered to pay 1/4 of the rental costs, saying that it was nice from me to continue the journey (As I could have just returned home with public transport but didn't), and it would be fair for all in my car to contribute, and that I already had to pay a lot for the repairs anyway. The other two, however, took everything for granted, and didn't contribute anything. Their point was, that I agreed to take them with me if they pay for their ratio of the fuel.
How to handle such problems? I took part in many similar trips, and we never faced any expensive difficulties. We also never made official contracts, it's just matter-of-course that for very short trips in and around our town we don't handle any finances, and for long trips we share the fuel costs.
Talking about exact monetary contracts in case of accidents and other unforeseen events might seem awkward in a casual setting. Would it really be normal to show up before the trip with a long list of possible but highly unlikely scenarios and debate which costs should be shared and which shouldn't, and then when it happens, argue and rules-lawyer about which category it really belongs to?
Just dropping them off then and there, and letting them find a bus or train home (while making them lose a lot of money for the already payed-for overnight stays, event tickets, etc.) would have been rude and unfair in my opinion, and it would have driven my costs even higher, with less people to share the fuel costs with. Just cancelling the trip might have been somewhat less rude in my opinion, but I didn't want to cancel it for myself.
The dilemmas above made me ask this question here instead of at money.se.