Many times if this kind of issue goes to court, the ruling will be a compromise that is intended to be something that both sides can live with, as opposed to a hard-and-fast interpretation of property laws.

Damages can be quantified by a contractor as long as a specific goal is specified, such as "how much to remove this road and regrade and seed" or "how much to establish a ditchline that will prevent further damage to my land". You may need quotes on materials as well, such as stone, seed, mulch, pipes, etc.

What if he wasn't using the road, though? Would you then fix it yourself? Court should be viewed as a last resort; if you have the means to fix it, and he doesn't, why not just explain to him you can fix it but you won't be doing his road maintenance for free? Maybe you can make a little money maintaining your own land to your satisfaction, and he will probably be saving money compared to having somebody else do it.

Good luck,
Bill

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