Ive done several commutes.

Dover to Northeastern 2 days a week. Wasn't so bad because I could drive during off hours. Straight down 95 was free and clear til I hit the on-ramp to Storrow.

Kingston to financial district 5 days a week. I'd drive to Haverhill and take the commuter rail into north station then walk the mile to work. This took a real toll. Had to get the earliest train to make it to work on time. I'd be up at 5am and home by 9pm. Horrible.

Exeter to North Station on occasion. This is my current "commute" to Boston and it's so nice. More expensive ride and fewer time options but the train is very nice and the wifi works well enough. I don't really go into the office but I usually go this route for going to the airport or just going to see friends. (Saw you're going to Longwood. This is a tricky one cause you can definitely get the green line from north station down there but it'll take forever. Honestly if you only go a few times maybe see how an uber or taxi is, may or may not save you time? Hard to say...)

All in all, get yourself close to an Amtrak station if you're doing infrequent visits. Or, if you have easy parking, see if you can do some staggered hours to make the traffic easier to manage. Whatever you do, I'd recommend avoiding the drive on 93. Gross. :(