Do theater and poetry readings count? My worst experience was when I was doing poetry readings, which I have stopped doing since. I usually read my own stuff on the microphone, but at some point I got involved into a two-men show reading the work of a famous local poet.
There were pretty solid differences between us two. The other guy was a poète maudit type of dude who did readings on a 3AM radio show that nobody listens, but he had a pretty strong idea of what he was doing, and has "his way" of doing thing, which to me meant a formulaic tone and empty articulation. I had none of that "concrete experience" but I had opinions to sell, including that he was a pretty crappy reader. So in the end I was the tenderfoot nag that had all the answers and was bossing around Mr Talent himself. Morality: if you don't like the work of someone else, don't even think of collaborating.
On the other hand, I was involved in high school as an actor and a director for plays, and although it was a rollercoaster of emotions (median age: 15), we all had a similar drive to get things done, so in the end we were proud of our results. Morality: stick with people who share your goals and don't waste time with loafers.
I haven't done any photographic collaboration so far, nor do I intend to because I consider I have much to learn before I can be comfortable working with anyone else but me. I would be comfortable having people doing related tasks (makeup, models, etc), but I don't want to have another shutterbug around me.