I just did a tour of hotels.com for Boston and not knowing your dates of travel put in the end of October through the 1st of November, and found hotels in the Boston area with rates of 150 a night down to 92 a nite (at the Roadway Inn in Newton) so there are some good deals available that you might check with your correct dates of travel.

Have a great time (Boston is my hometown)

The 3-day visitors pass costs $18. Of course you should believe the transit site rather than the AAA book! The rates went up in February. Since a regular ride on the subway costs $1.25, you would have to ride it 15 times in 3 days, that's 5 times per day (not counting the commuter rail), in order to break even.

Please don't get your hopes up too much for "conversation, people, and views" on the commuter rail to Franklin.

I'm totally confused by your comment about meeting your son in Boston -- I thought he was coming from VT to Milford to meet with you? Now, are you both going to be journeying to Boston? Could you have him pick you up at the hotel?