I've been to several of these places and I just don't hold them in the same esteem as you do, but there's nothing wrong with that. I will say the walk from the T station to the Tipsy Toboggan is a bit of a haul and not very scenic, while hoofing it to Columbia Rd really seems like a long distance for not much payoff. As an aside I had the pleasure of camping out overnight on the USS Massachusetts with my boys scout troop and while it was uncomfortable as all hell the staff did a really good job. I recommend trying it...once.
It's easy to dismiss the USS Massachusetts for precisely that reason--"oh, it's just an attraction for Boy Scout troops"--but I contend it's an amazing (even if not possessing the most slick and sophisticated "production values") WW2 museum, with some haunting memorabilia. I'll always be struck by seeing, in its gallery of wartime media artifacts, a framed Life magazine cover from 1943 or so, at the height of the Nazi terror machine, featuring Himmler superimposed over a graphic of hundreds of skulls. The caption: "Europe's Policeman."
Also, if you have the chance to visit the USS Alabama in Mobile Bay, it's a similarly awesome spectacle. (When I was there in late March, conditions were already getting oppressive, so it's probably best done between Halloween and St. Patrick's Day)