I have a question for clarification before considering answers.

You begin by describing yourselves as "first timers going down this path". In your second question you mention "dues and assessments from previous years".

Was your association originally formed using the Private Ways Statute, § 3101, Call to Meeting, so that, throughout this time, it was and is a Statutory Road Association?

Since there is no certifying Registry for Statutory Road Associations, your association written records such as By-laws, Records of Meetings (Minutes), and Notices to owner/members are key to proving compliance with the Maine Private Ways Statute (23 MRS § 3101-3104) when collecting maintenance fees in default through Notices of Claim. 

If you have records to support your Statutory compliance, I believe you will be successful under § 3104, Penalties and Process, if not, then a judge or opposing attorney may consider your process less than "fair and equitable" to owner/members and cause your claim to be denied.

You ask a few questions in your initial post. I will answer assuming that you are successful in finding written records to confirm that your association is a Statutory Road Association. 

Question 1: According to § 3101(3), email notification may be used if (written) permission is granted by the receiving owner/member. If permission is not granted, USPS to the address of record for the owner at the Town tax office is sufficient. We use certified mail, return receipt requested, for problematic owners.

Question 2: As long as the delinquent owner was notified of Meetings 30 days in advance with agenda including the amount to be assessed, given the results of voting, and a firm due date(s), you may initiate advanced collection procedures set forth in § 3104, including Notice of Claim for assessments "more than 90 days delinquent" at any subsequent time. I am interested in other views here.

Question 3: In our By-laws, we give our Board of Directors responsibility for deciding the policy on late payment penalties. We want our policy to be seen as "fair and equitable" by the court at collection time. Currently, our Board assigns a 5% late payment charge on the assessment 90 days after the due date. We also begin charging the delinquent owner the interest rate levied by our Town tax office (currently 8%) on the unpaid balance. We include a statement of our late payment policy in our Notice of Assessment for each meeting.   

Doug -

For an attorney, have you tried Mary Denison of Lake and Denison in Winthrop? She's an expert on road association law, which is a specialized area that most attorneys are not familiar with. If she can't take you on, she may be able to recommend someone else who can.

I'm curious - if you have no documentation, why does it seem your Board was sure that you were a statutory road association? If your bylaws note that the association was formed in Feb 2000, is there no copy of an initial notice sent out by a notary? Is it possible any past officer or anyone who was a member from the outset would still have a copy of the notice filed somewhere? Or could you check with local notaries and see if you can find who did the initial notice?

If there is no proof that the initial meeting was called by following the steps required under section 3101, then you probably don't have much other choice than to go through that process now. In that case, you can only use the section 3104 Notice of Claim process to pursue non-payers for what is owed from the time you officially become a statutory road association. However, you could try Small Claims Court for amounts owed up until now. I can't guarantee how successful that would be, but since it can be done without an attorney, it shouldn't cost much to try.

One caveat - you would need to make sure the Judge understands how the law works, and specifically, that sections 3101 - 3104 don't apply. I believe it would be more like a mechanic's lien, to recover payment for services rendered, or it might be deemed "theft of services." I know of one case where a non-statutory road association tried to recover a few thousand dollars of overdue dues from one member who had not paid in several years (and apparently not due to an inability to do so.) The judge tried to apply section 3102, which should not have been relevant because they were not a statutory road association. But the judge misinterpreted the law, thinking the 1% limit meant they could only recover 1% of what was owed. The 1% actually only limits the amount of dues that can be charged per year to 1% of the municipal evaluation of the parcel of land. So for example, on a piece of property valued at $50,000, a statutory road association could charge no more than $500 in dues each year, and if the owner had not paid their dues for four years, the road association should have been able to recover the full $2,000. Instead, that judge would have granted them only $20, due to a mistaken interpretation of a law that didn't even apply. In fact, since they were not a statutory road association, they were not even bound by section 3102, and could theoretically have charged more than 1% of the municipal evaluation. As one road attorney told me, Maine now has so many laws that no judge can be familiar with all of them, so the ability to clearly explain the law to the judge can make or break a case.