Aside from the Venner Rd article (Article 20), the remaining articles are 38, 39, 56-67, for a total of fourteen.
Articles 38 and 39 are the collective bargaining ones, but since the word on the street is that there are no pending agreements, Article 38 will likely be a quick “no action” vote after a brief explanation of where negotiations stand, and Article 39 will be a quick vote to set aside money to fund the agreements when they ultimately happen.
Article 56 (appropriation for Minuteman Senior Services) may draw some discussion, since FinComm recommended no action, as may Article 58 (appropriation for 200th Anniversary Committee) because FinComm recommended $1,000 but the committee wants $6,200. Articles 57 and 59-64 are routine and will likely be voted on with little or no discussion.
Article 65 seems uncontroversial to me, though if some built-up resentment was behind the filing of the article (I have no idea if there was or not), then there could be some venting. That aside, I can easily see it being voted with little discussion.
Since (according to the BOS report) there are no obligations on the Town or property owners to have pieces of Mass Ave declared a scenic byway, Article 66 should also not take up much time.
So the drivers will be Article 20 (Venner Rd) and Article 67 (Anti-spanking resolution). I think that if the Venner Road matter is concluded by 22:00, we will finish on Monday because the remaining hour will leave enough time to get through everything else and begin debate on Article 67. With Article 67 underway, I believe the meeting will turn down a motion to adjourn at 23:00 and instead will stay and finish the meeting rather than come back for a short session on Wednesday. Staying late may well happen even if Venner Road goes past 22:00, maybe even to 22:30.
As for Article 67 itself, I think either debate will be terminated very quickly (for example, a “pro” speaker, a “con” speaker, and then the motion to end debate — as happened with the Anti-spanking resolution back in 2003), or will go on for a long time. I don’t think there will be a middle ground.