Chuck - Good work - that's coming along nicely.  I did pick up one spelling error, in Article VII - benefitted needs 2 "t"s.  

I noticed that you said your annual meeting will be held "on or about June," but payment is due July 15.  In light of the need to allow time to get the bills out and time to return payment, did you mean to specify an approximate date in June?  Otherwise, I would interpret "about June" as meaning it could be as early as late May, or as late as early July.  Or would it be better to make your July date similarly flexible? 

We hold our annual meeting the first Sunday in August, send the bills out within 30 days of the meeting, and allow 30 days after the date of the bill for payment to be returned.  Then we allow another 30 days grace period before the late fee and interest kick in, during which we can send out a reminder if needed.  So the other dates are all tied to the date of the Annual Meeting, rather than being pinned down.  Sometimes the first Sunday in August isn't convenient for everyone on our board, but we're stuck with it because it's in our bylaws.

Other than that, I wholeheartedly agree with your desire to keep it as simple as possible.  People are more likely to actually read them and therefore abide by them if they are short and sweet.   (I keep saying that if we all obeyed the Ten Commandments, the Maine Revised Statutes wouldn't have to take up two shelves!)  Besides, I think it's the little details that are more likely to become problematic and need to be amended later.  If you're a bit vague, it leaves you more wiggle room.

I also applaud your desire to avoid spending money on attorneys instead of on the road.  While the occasional consultation can save you money in the long run, I have seen people turn things over to attorneys that could have been handled for much less by other means.  (i.e. by an accountant, a mediator, or just working things out face to face.)  As Attorney John Cunningham noted at last fall's MARA conference, if it costs you more to take someone to court than what you "win," you haven't really won.  So he sees his job as trying to keep people out of court.   (It's that sort of advice that makes me have such high regard for John!)  He went on to point out that if someone hires an attorney to sue you, you want that attorney to look at your bylaws and tell them they haven't got a case.

Our own town is a prime example of funds going to an attorney instead of repairing a road.  (Not the town where our road association is, but the town where our year-round residence is.)  Years ago, when they told us our "discontinued" road was a "public easement" which the public could use freely (including logging trucks,) we asked if they would repair the damage the log trucks did, or even just order the logging company to do so.  We would have been happy with a few loads of gravel in the bad spots in just the half mile up to our house, and an annual grading.  But they said that would set a precedent, and that their town ordinances would require them to bring the entire 1 1/2 miles of road up to full town road standard.  So instead of putting a couple of thousand dollars into the road each year, they poured tens of thousands of dollars into taking us to court to prove that it's a public road they don't have to maintain.  What do they have to show for it?  Nothing went into road repair, and the road is still a problem, 35 years later.  It would have made more sense to change their ordinance to allow them to just make the road passable.  The increased tax revenue from development of abutting properties would have paid for it.  Sorry for the rant - I probably should just have said you're wise to want to put your money into the road instead of into attorneys, and left it at that!