Supported tours kinda take the fun out of it for me, but I did the transam this past summer with a group of 5.
We all were comfortable with soloing if it came down to it, though some hadn't toured before, so we had the mindset going in that if there was conflict, no worries and we'd be on our way, which in my mind is a good way to be.
In any case, we had very few conflicts, many many inside jokes, but at the end we did hit a sour point. When we hit Eugene, 3 were headed north (Astoria), and 2 were headed south (San Francisco) So we made the decision in Eugene that we'd stick together til we hit water (Florence). One of our crew heading north wanted to do the original transam, which cuts a bit of the coast off in favor of Salem I believe, but in the end he agreed to go straight to the coast. I was the one who really wanted to stay together from coast to coast, or at least the spokesperson for the idea. In any case the day we did hit the coast there was a northern wind at about 35 mph. He got so frustrated that he would have to bike north the next day that he lashed out at me about it and blamed me for his potential strife. In the end, the wind actually turned out to be fine (southern actually) the next day, and realistically it only added a day on the coast either way. Unfortunately it put a sour taste in everybody's mouth the last day we were together.
Had a good ride after that, and we're fine now, but at the time it was pretty upsetting.