query: has title insurance ever paid off on an easement dispute

Easements are one of the most common exceptions to coverage - UNLESS - you see the words "together with" in the legal description. If you see "together with" or some other language citing the easement in the legal description in the policy, then the insurer has INSURED that you have rights to the easement. If the only reference to the easement is found in exceptions, it likely is not covered.

In the case of shared driveways, it really depends how they were set up. If I can see a clear legal right of use, I will insure the right. If not, the only mention of the driveway is as an exception.

In our area, the access to the land is insured from a public roadway. That access may or may not be on and over the shared driveway.