Well, if that's his premise, he is misinterpreting the statute. Although many people refer to the "Notice of Claim" as a "lien," they are not the same thing. A lien is a specific process that follows a time schedule ending with taking the person's property if they don't pay. There was a court case a year or two ago in Minnesota where it was determined that it's unconstitutional to apply property tax liens in the way that many states - including Maine - have done for years. It has been common policy for a town to file a lien against a property that is behind on their taxes, then take the entire property even though the amount owed was only a fraction of the property's value. Then the town sells the property, likely for much less than it's worth but much more than is owed, and keeps the profit they make on the deal. That was declared unconstitutional. The town should only be able to take enough to cover what is owed. The rest of the property should remain with its rightful owner.
The Notice of Claim process, on the other hand, does not end with taking the person's property. The claim simply sits at the Registry of Deeds as notice that the person owes a debt for the value which they have received in road maintenance, which they have not paid for. If the person tries to obtain a loan or tries to sell their property, a title search will bring up the Notice of Claim, and the debt will have to be paid before the loan will be granted or the sale goes through. They will not have their property taken - they simply have to pay their debt, plus whatever other costs and interest may be attached to it. Since he is enjoying the benefit of the road maintenance without paying for it, I would think that could be considered theft of services.
I suppose he could argue that he never asked for that service, didn't want it, and should not be forced to pay for something he didn't want. Sort of an "unfunded mandate." But if he had to chance to vote and didn't do so, how is that any different from not showing up at Town Meeting to vote down an increase in the budget, and then complaining that your property taxes went up?
If there is a hardship involved, that's certainly understandable and the Association could show compassion by having everyone else chip in to cover his share. But if this is just for sport, seems like it won't take many hours at attorneys' rates to amount to more of a bill than the road association assessment.
One final note - do be careful about your terminology. Under Maine statutes, 23 MRS section 3021, a "private way" is a "public easement." Even the road association statute, 23 MRS section 3101, now uses that definition of the term. But the road association statutes apply primarily to "private roads," not "private ways," and I believe what you have is a "private road." Unfortunately the Maine statutes do not define that term, and that's one of the problems the Commission on Abandoned and Discontinued Roads has been assigned to work on. I would like to see "private road" defined as a road that is privately owned and maintained, and over which the owner or owners may restrict public use or passage.
The confusion is magnified by the fact that sections 3101-3106 come under the subchapter heading, "Private ways," left over from earlier statutes. The only reason "private ways" are still included in sections 3101 - 3106 at all is because there are some private roads that have been designated as "private ways" (public easements) so that there is public use allowed, creating a public purpose and therefore allowing the Town to provide snow removal. Otherwise the town would be prohibited from expending public funds for the private purpose of maintaining a privately owned road.
If your road were in fact a "private way," (meaning a public easement,) then I would argue that there may indeed be questions of constitutionality because private citizens should not be forced to maintain public roads for the use of the general public at private expense.