I thought about elaborating on that, but every other question I came up with started to show my own prejudices; I'll leave it more open-ended and give you a chance (if you'd like) to riff on the future of Wikipedia.
I think about Wikipedia in terms of the Greek Fates (or, more accurately (and this will highlight just how much of a total loser roleplayer I am), the Garou Triat of Wyld, Weaver, and Wyrm). The one who spins new thread, the one who weaves the thread into useful fabric, and the one who clips excess thread. The editor who creates new articles on interesting topics they've found or adds new content to existing ones; the editor who formats them to standards, revises them, organizes them into categories, and finds citations for them; the editor who scrutinizes them for notability and deletes or redirects the unacceptable ones.
In the beginning there was mostly content creation. Then came the other two kinds of editors, and shortly thereafter there were admins and bureaucrats - editors who wove or clipped other editors rather than articles themselves. From anarchy there arose a massive tangled bureaucracy - which, having grown organically rather than along any kind of plan, looks to the average outsider like a Gordian knot.
Well, it remains to be seen whether we can have a proper balance between the weavers and the cutters - a stable, long-lasting one. In the cosmology of the Garou, the Weaver went mad with her thread and ensnared the Wyrm, who also went mad with destruction, and because of the struggle between the two, the Wyld is dying out. On Wikipedia, all the arguments about notability, citations needed, issues of format, following of procedures and protocols and so forth are driving away the spinners.
Some of the spinners are simply surprised and confused to find structure where they expected chaos, while others have trouble wrapping their minds around the prevailing paradigm (that is, it's not about editors, it's about articles). Even aside from those, however, many would-be spinners (and some would-be weavers) take one look at the Gordian knot and just turn around and go away.
Can the bureaucracy be woven into a useful tapestry that helps more than it hinders? Or do we need a hero to come along with a sword? I don't know, but I lean toward the former much more than the latter.
How Now Wikipedia?
Editting for Wikipedia is a lot like making sandcastles. At any moment, a big wave might come by and revert your masterful work of art to a pile of sand.