I understand your "catch 22." But I think the answer lies in the exact wording of the statute. Title 23 section 3101 (2) says, "When 4 or more parcels of land are benefited by a private road, private way or bridge as an easement or by fee ownership of the private road, private way or bridge, the owners of any 3 or more of the parcels, as long as at least 3 of the parcels are owned by different persons,..."
I think that indicates that the statute gives more importance to the number of different owners than to the number of parcels. So for the initial vote, I think each owner should get only one vote, even if an owner has multiple parcels. Once you have succeeded in getting enough votes to form the association, then if you need to refine your definition of "parcel" to fit your specific circumstances, you could do so.
Another consideration is whether the definition of parcel is actually likely to produce a different outcome in the initial vote. If you have ten owners present, one of whom owns two parcels, and the other nine agree that they want to form a road association, then it's not going to matter whether you give the owner of two parcels one vote or two. His vote won't change the outcome. If the nine are divided, the tenth person's one vote or two votes could tip it one way or the other. But if you're a brand new subdivision where one developer owns a dozen parcels that he has not sold yet, and the only other owners are five people who bought parcels from him, then if the developer disagrees with the other five as to whether or not to form an association, it would obviously make a huge difference whether you gave the developer one vote or a dozen votes. In that situation I'd go with one vote per owner, and if the developer objects, I'd point out that if each lot is a parcel, he will owe a dozen dues payments.