Shane, that's me with the half barrels. It works very, very well. If you haven't done it, head on over to Donkey's board and read all you can about "bells." You'll find a lot of solid info on larger chambers for mass. Here's a starting point:
http://donkey32.proboards.com/index.cgi?board=experiment&action=display&thread=40
You've got a pretty good handle on some of it, the trade offs regarding mass vs. size. In some spaces it's an advantage, in others not so much. Depends on what you are going for. I've helped on a few half barrel system builds in dwellings at this point, and they work great for folks who need to spread the mass load over a larger area due to floor construction or layout. They are also great for areas where you want quick response and don't need the long term storage. Keep in mind half a 55 gallon barrel is only around 11" high. With a 2"
cob layer underneath, you would have 5" of cob over the top to reach seating height of 18". That 5" is only that thin in the center, it rapidly gets thicker towards the sides as you build out. You can get a LOT of mass built up on them if you choose to. Not only that, but a regular width bench is hard to heat with a single run of 8" flue, you'll typically see the runs double back in a bench that is 24" + wide when using flue pipe, so while they still hold more mass than a larger chamber, the difference isn't quite as great as you are thinking.
I think your large flue would work really, really well for some applications, give it a try. You can agonize mentally over this stuff forever, the best way to learn is just start throwing systems together and see how they work. Mud is free. Good luck on your builds!
Oh, edited to add that if you go with that 20" pipe, I'd cut it in half if I were you. Easier to achieve seating height and the bottom half of the pipe will most likely not transfer much heat to the mass. Just a thought.