We have about 100 lot owners in our nonprofit corporation. About 90 pay for year round maintenance of our roughly 4.3 miles of road. Year round residents pay $500, seasonal $ 350, and lot owners $75. Those that don't pay are taken to small claims court and a notice of non-payment is attached to their deed. This has worked well for us for 2 years now.

Our road association is small - 12 landowners. All lots in our subdivision are owned lots. Of those lots, 

5 are not yet built on & 7 have existing homes.

Of the 7 homes, 3 are year-round resident. (One of those is for sale while living in it)

Of the other 4 homes 2 are for sale but vacant.

Of the remaining 2 homes, both are vacation homes.

One of the vacation owners visits on a regular basis on week-ends and 1 week during the summer.

The other vacation owner uses it for snowmobiling for 3 months and visits several times during the summer.

Therefore, for us to try and determine a fair amount of dues based on usage would be a nightmare! Lots get built on and then you have to re-evaluate the dues process again.

Then there is the dues based on road frontage. That is the most fair way in my opinion but then you would have the potential for some vacant lot owners paying most for their small lot next to a lot that would pay the least for their largest lot that has a home on it and uses it year round. So when really thinking that through, it does not sound that fair after all.

So, we go by what the law recommends and that is to base it on per lot owner because the term in the term says "is benefited by". That means that each landowner has the benefit of a road being there to reach their property any time they wish or as often as they wish.  

You might want to check out the question about Municipal Value of Lots in Tree Growth.  The answer by Cliff Goodall gives an excellent explanation of how the 1% limit should be derived.

As for deciding which lots pay what, I remember Cliff saying in a past year's MARA workshop that the "fairness" clause in the statute has been interpreted by the courts to mean that whatever formula you come up with, it should be applied equally to everyone.  So if you say every lot pays the same amount, that is what is fair under your formula.  If your formula says lots with houses pay one amount and lots without houses pay another, then as long as you apply it equally, that is also fair.