"What are some of the negatives involving an agreement such as a private road / shared driveway? we only have one way in and out."
o How do you allocate the costs of maintenance? For example, if the road is 500 feet, and there are 5 homeowners, does each pay 20% or do you charge the homeowner who lives at the end more? Is it fair to charge the homeowner who lives 50 feet from t road entrance the same as the one who lives 500 feet from the road entrance?
o How should repairs be charged? Even if you charge homeowners the cost of maintenance in a manner that reflects the distance on the road they use, should the same or a different allocation apply for repairs?
o What if damage is caused by a particular homeowner? Shouldn't that homeowner bear the cost? If so, how do you define what is damage caused by a homeowner versus general damage?
o How do you determine if the road should be taken over by the town and be made into a public road?
o How and when should fees be collected?
o What happens when someone doesn't pay the fee they are assessed?
o Where is the money to be kept? Which bank? What name?
o How should disputes be settled?
o How are vendors (e.g., snow plowing) selected?
Be sure to hire an experienced real estate lawyer to help you work out the agreement.