I will absolutely be going over all the details with my lawyers before we finalize anything. I don't think that the restrictions on political speech are all that severe for non-profits. For example, Consumers Union is always making political statements in their Consumer Reports magazine, calling for increased regulation of this or that product category. And National Geographic magazine has editorials.
I think you're just barred from campaigning in particular ways for particular candidates. It seems unlikely that Wikipedia/Nupedia would run afoul of that kind of thing.
<political commentary> McCain's "campaign finance reform" bill is a disaster on this front, as I understand it. Nonprofit organizations like Greenpeace or the NRA would be barred from running advertisements about particular candidates for 90 days before an election. This means that voluntary organizations designed to empower individual political speech would be blocked from their primary mission. Supporters of those organizations would lose the ability to effectively make their voice known.</political commentary>
Part of the purpose of doing a nonprofit is to make it "comfortable" for other people than me to contribute money to the project. Right now, I pay all the bills, which is fine for now, but someday this will grow beyond my capacity (or, my capacity may diminish!), and I certainly don't expect that anyone will feel comfortable signing on to donate money to my for-profit company. :-) Of course, if you feel like donating money to Bomis, by all means, let me know and I'll make sure you have the right address. *wink*
But when Nupedia and Wikipedia are spun off into an entity with a non-profit charter, I think people will feel comfortable signing up for "sponsorships", in the same way that people support local theater groups by becoming patrons. You could be a "Bronze level" supporter for $X per month, a "Silver level" sponsor for $Y per month, a "Gold level" sponsor for $Z per month. All funds would go toward the improvement of the project.
That's just an idea, but I know it can't happen as long as I'm personally funding everything within a for-profit company.