is it totally insane to drive around Boston? I'm bringing 3 kids and a stroller- how hard is the public transportation option? How far is it to the kosher food? Is parking that crazy in and around the attractions areas?
It's not the driving that's the issue, it's the parking. All of these hotels charge an arm and a leg - though that's unavoidable if you're driving to Boston in the first place. And parking by shul/food is fine too - at worst you're talking about waiting a little for a metered spot. It's the attractions that are problematic. The areas where most of the attractions are have basically no street parking, and garages are expensive. Where do you plan to go specifically?
Yeah, it's pretty rough. What are you planning on doing? Maybe some of the locals can chime in regarding kids/stroller on the T.
Most of the kosher food is on Harvard St. If you're driving, it's maybe 10 minutes from HR Cambridge, 15 from Sheraton, and 20 from HR Boston. Assuming you're paying for parking by the hotel (whichever) with in and out privileges, it's probably worth driving, even if you can get there on the T. The same can't be said for attractions.