One of the things we talked about at the MW dev summit recently was the need to have a clearer roadmap of what's being worked on, what's going to be worked on, and how that's going to fit in with third-party users as well as Wikimedia's big sites.
I've started putting together a 'mind-map'-esque roadmap diagram, currently in a Google Drive drawing:
https://docs.google.com/a/wikimedia.org/drawings/d/18fpigtf0mXIu9ShvJmqEQJvX...
This is open for commenting but not for editing as I don't quite trust Google's versioning tools. :) But I would love more feedback on this, especially for third-party goals that we (WMF Engineering) may need to support or plan around even if we don't do it ourselves.
Currently the diagram contains some major projects being worked on at WMF or WMDE already (color coded green), plus blue boxes for things that seem to be popular ideas already, purple for stuff I think might be awesome, and red for some crazy stuff that I still think would be awesome. ;)
The projects are roughly divided up horizontally by area and vertically by depth/relation.
Please note this is a preliminary document and should not be taken as WMF plans or endorsements of which projects will get done (even when it's complete it's going to include some "maybes" and "crazies" :)
If a major initiative seems to be left off don't be offended! Let me know and I'll try and work it in the map. :)
-- brion