Wikipedia also keeps devoting significant screen space to asking for more donations from time to time even though they have more than enough money to keep the site running indefinitely. Should donations dry up with they reduce their (largely non-Wikipedia-related) expenses or will they just get more agressive in asking for moeney?

Wikipedia is probably in a strange problem where they have more than enough money (they do have a lot of staff though?) and really we would want them to keep going for hundreds of years, so I think it is good for them to keep an enormous runway. We can't trust governments to fund it, as it may not say nice things about those governments and they may want to change that. And by they I mean the USA which would probably end up being the biggest donor and thus get veto powers.