Thank's for the detailed explanation! I have a warm spot in my heart for Dulles, because it's my first memory of American (we flew into Dulles from Bangladesh in 1989). It's really convenient if you live in Great Falls or Reston. And I loved what was then the semi-rural Virginia around the airport. But agreed, it's a huge pain in the butt to navigate.
For all the hate EWR (Newark) gets, I much prefer to connect through from there to Europe from Boston than Dulles. My biggest objection to EWR is that it's a PITA to get into Manhattan from but, then, that's pretty much true of all the NYC airports. I'm rarely doing that though as I'm almost always taking the train into the city.