It has worked well for me. 8 years ago I met a Russian guy in a forum and we've created several products together and been reasonably (though not stratospheric) successful. We only met, for the first time, two years ago. Sometimes it comes down to gut instinct, even thousands of miles away. We couldn't do it without the technology, but it works really well with it.
One interesting point is that we get on better remotely than I ever think we would if we were in each others faces day-in-day-out
After seeing your iChat video + Trac setup working at your co-working space, I went looking for a collaboration setup for our remote team (Trac just never did it for me.)
We've settled on Google wiki + Lighthouse integrated with GitHub. We're also testing Campfire for "watercooler" team chat (when IM isn't necessary)
One interesting point is that we get on better remotely than I ever think we would if we were in each others faces day-in-day-out