What if WordPress sent a message back to WP HQ? So that we could count installations, and possibly create maps of WP users or some such.
It would just send something saying the URL of the installation, and possibly any GeoURL info you've supplied, once a month or something? If that sounds too invasive, then an MD5 hash (it's one way, and doesn't contain any data that can really be used to identify YOU) of the same info could be sent instead (so that we could prevent counting the same install twice) and any IP information we recieved could be discarded. That way your priacy would be maintained, and we'd still be able to count our install base.
So? Any privacy concerns? You can always just not turn the feature on.