Sorry for the discontinuity in the thread in the mailing list. I wasn't signed up the for mailing list before sending the first message, and I can't figure out how to reply to an archived message. Doing my best with copy and paste.
First - thanks, Lorenzo. Your message caused me to re-affirm that I was doing the right thing in the code and that I must have made a mistake somewhere else.
For any interested - As it turns out the problem was simple testing/operator error. I was testing with Firefox and trying to go to the same URL from 2 tabs at the same time. I wasn't seeing the request getting processed in the server because -Firefox- was serializing them (that is, starting the second request only after the first request returned). I assume it was just trying to be helpful since the URLs were the same, expecting a cache hit for the second request or something. I just wasn't expecting that behavior and after numerous attempts, assumed the problem was in my webserver code. I'm guessing other browsers would behave the same way. I feel a little foolish for not figuring this out earlier, but that's the way it goes.
In any case, like Lorenzo, I can now confirm that microhttpd will work quite well with long-polling if you want to roll your own solution. If you do some stuff to keep track of sessions (via cookies), you can also detect multiple 'comet' requests from a single client and respond accordingly (moving to fast-polling to prevent locking up browsers that only allow a couple connections to a single server). You have to handle all this yourself, of course, but it can be done without too much trouble with some smart locking/waiting/timeout code and a reasonable protocol back up to the browser.
For any finding this from a search, you could also consider using the Bayeux protocol (from CometD). I don't need that generic of a solution so I don't want to mess with the complexity, but I see no reason why you couldn't make that work if you were so inclined. Understanding the ins-and-outs of comet prior to rolling my own solution has been helpful for me. Also - for those thinking about CometD - while I miss the feature-richness you get from pre-made Java-based webserver solutions, I have really enjoyed the speed and control microhttpd provides, and I do not regret the choice to use it at all - especially on an embedded system.
Ken