There's this wonderful idea called "Do-ocracy" where everyone understands that the people actually willing to do things get all the say as to what gets done. ... Our democratic training has taught us to think this idea is a recipe for totalitarian disaster.

I can't speak for your democratic training, but my democratic training has absolutely no problem with acknowledging merits and giving active people trust proportional to their achievements and letting them decide what more should be done.

It has become somewhat fashionable here, in the Moldbuggian vein, to blame community failures on democracy. But what particular democratic mechanisms have caused the lack of strategic decisions on LW? Which kind of decisions? I don't see much democracy here - I don't recall participating in election, for example, or voting on a proposed policy, or seeing a heated political debate which prevented a beneficial resolution to be implemented. I recall recent implementation of the karma penalty feature, which lot of LWers were unhappy about but was put in force nevertheless in a quite autocratic manner. So perhaps the lack of strategic decisions is caused by the fact that

• there just aren't people willing to even propose what should be done
• nobody has any reasonable idea what strategic decision should be made (it is one thing to say what kind of decisions should be made - e.g. "we should choose an efficient site design", but a rather different thing to make the decision in detail - e.g. "the front page should have a huge violet picture of a pony on it")
• people aren't willing to work for free

Either of those has little to do with democracy. I am pretty sure that if you volunteer to work on whichever of your suggestions (contacting meetup organisers, improving the site design...), nobody would seriously object and you would easily get some official status on LW (moderator style). To do anything from the examples you have mentioned you wouldn't need dictatorial powers.