Well this thread turned out bigger (and much more productive) than I
expected!
To my mind, Wikimania continuing to happen every year is a minor miracle,
and one that's only possible with the hard work and dedication of lots of
people.
However, it's a miracle that isn't without its problems. The most obvious
problem to my mind is that there is a very mixed quality of actual
conference programme, and without clear objectives (or at least not
consistent objectives). The Wikimedia Conference, by contrast, has a much
clearer alignment of the programme with a set of goals, and work happens to
follow up before and after the conference.
The second problem is that the responsibilities for governance and
management of the conference are really very unclear. We have the Wikimania
Committee, we have the local team (and in some cases a local chapter who
may or may not be working closely with the bid team), we have the Programme
Committee and we have the WMF. (Actually we have the WMF at least twice, as
the priorities of the WMF team involved in organising the conference don't
always seem to align with those of the rest of the organisation).
In my view, the most useful thing for all these groups to do is to work out
who is actually responsible for what, and document it, in public.
Chris