re: Advice on starting a road maintenance fund?

How is the road owned? Does each family own a portion of the road? Is the road subject to some sort of common easement? Is the road part of each family's property?

I can think of a few options:

1) Set up an LLC, make each family a member of the LLC, and get an LLC account to handle everything. However, for the amount we are talking, it might not be worth that.

2) Talk to an escrow company and see if they can set up some sort of account for you, in which the company bills each family, and there is some sort of agreement required to expend funds.

3) Have someone pay for the entire repair, with notes signed by the other families to repay the monies.

I must say, it kind of sucks that you have concerns that your neighbors would either steal the money or not contribute their fair share.