Originally I wanted to post this as a comment at the blog for a proposed Wikimedia Pennsylvania Chapter but it doesn’t allow anon comments (grmbl, there are cute captchas and the like). So I post it here:
I totally support the idea of locally involved Wikimedians but I think that a regional Wikimedia sub-chapter can only be the the last step if needed at all. There are many more important steps in advance:
At first: Why not just joining the Wikimedia Foundation as a (support) member? Regretfully the Foundation web site doesn’t give any useful information how to join formally as a real member (well we are all Wikimedia volunteers so the point on their web site is nothing new). This is a pity as a large scale official (support) members would maintain the role of the Wikimedia Foundation as grass root based and not going into corporate whatever and of course regular financial contributions by support member fees mean a constant and reliable source of donations (of course this can only be one part).
In contrast for example the Wikimedia Deutschland e.V. directly encourages people to join and get an official (support) member and people actually do so and Wikimedia Deutschland can partly base their expenses on member fees. And of course every member can publically say that he is a Wikimedian, which in turn opens doors in circumstances you mentioned.
So my advice is go and persuade the foundation to make it easier to get an official (support) membership and you won’t need a regional chapter anylonger.
The next thing are regional meetups: A brief look into Wikipedia:Meetup reveals that there is a huge distance between different US meetup cities and of course people don’t seem to meetup regularly.
In Germany (but also other German speeking countries) Wikipedians meet regularly and in quite some cities and towns. See Wikipedia:Treffen_der_Wikipedianer for a comparison. Each regular local meetup has its own page and people organize themselves rather efficient around that scheme.
And of course IMHO these very much interconnected regular local meetups are one of the secrets why the German language Wikipedia is the second largest (although languages like Spanish and French have a much larger potential). At local meetups people freely discuss their new ideas and past projects, start new projects like joined sightseeing for new free images, organize workshops and new article projects and motivate each other.