Both the D2000 and HE-400 have a hole in the upper midrange, so there's not much the HE-400 will offer you there, although it has way better instrument separation throughout its entire sound signature thanks to a much cleaner bass.
In your particular case, the biggest reasons to move on from a D2000 to an HE-400 would be if you were unhappy with the bloated nature of the D2000's bass and its masked lower midrange.
HE-400 being bass-lite or not moving from the D2000 depends on you as well. I personally used and loved my D2000 for a little over a year before I moved to an HE-400, and didn't find its bass lacking at all. Some feel it's lacking though. HE-400 is one of the bassiest and most impactful open headphones around though, so if you do happen to audition it and find its bass lacking, there won't be too many other open headphones that will satisfy you.
Comfort with glasses might be a potentially big issue. The old velour pads are the go-to pads for the HE-400, but they have really stiff foam, which could press the glasses into your head more than you would like. I have not experimented with the Hifiman focus-a pads with the HE-400, however.