There is no doubt there are some points the Wikimedia Foundation needs adress in the future if they don’t want to loose contact to their basis – their more than 700 different Wikimedia communities.
Do you want to act globally or locally?
Define the role of the Wikimedia Foundation. Do you want to be an international organisation that is only concerned about maintaining the multinational Wikimedia projects and multinational events such as Wikimania or do you want to be a local grass-root Wikimedia chapter in the US, too? If you decide against beeing the US branch of Wikimedia please encourage and support people actively founding a US Wikimedia chapter. There is a strong desire of US people to organize local events and who need backing and help such as info and promo material, logistical support or just a Wikimedia membership in order to do their local work best. The current state is a severe problem for the US Wikimedia community.
Don’t aim for perfect solutions.
The Wikimedia server administrators and MediaWiki developers have done a good job at making our servers more stable and reliable. This is definitely a good thing so I want to say a big thank you to all developers. But there are some things stalled for ages, which are ready since a long long time. Just two examples: The new Wikitex engine that provides features desperately needed since ages such as music markup in MediaWiki and single login, which is desperately needed for all people that work across languages and projects (not to mention the fact that maintaining the election is easier and more logical with single login). Do not aim a solution without any problems which is impossible, find a good compromise between technical stability and bold improvements. Both named features will have their side effects but we wouldn’t use wikis if we couldn’t sort them out quickly after we activated them. So Wikimedia Foundation please encourage your people and developers to a bit bold again sometimes (of course not so often like in the beginnings ;-).
Inform people what is going on
The easiest way to keep people informed is encouraging local wiki project people to write a regular summary about what is going on in the Wikimedia Fondation and in MediaWiki. There are already some really helpful efforts such as the Wikipedia Signpost, the Wikizine and Projektneuheiten (technical information letter in de.wikipedia which keeps people informed about technical changes). Encourage even more people translating them and contributing to them. Create a tutorial how to do so for people that want to keep others informed and link it prominently in an appropriate place. And although it is a bit time until the next election: Think about ways how to inform people actively and individually that are allowed to vote about the upcoming election. Every big real life election informs the people individually about such things for a very good reason.