Just a couple of basic ideas for you to ponder:
Travel styles differ greatly. The more you and your friends can agree on in advance, the fewer surprises and therefore the less likelihood of conflict. This includes issues like price, quality and style of accommodation; speed on the road and frequency of stops for fuel, rest, recreation and sightseeing; travel as a group vs. splitting into two or more groups or individuals; handling repairs and flats; decisions about routes, destinations and distractions on the fly; preferred riding surfaces (dirt, gravel, sand, pavement, etc.); hours riding and distances covered per day; departure and arrival times each day; group gear (e.g., how many tool kits, tire pumps, GPSs, spare parts, extra fuel, food or water to carry); differences in the need to plan every detail in advance vs. enjoying improvisation and the unknown; and how to handle splitting up the group if or when different desires, abilities or frustration tolerance arises.
There's lots more, of course. If I like to ride 600 miles per day but the group consensus is 200, I can still be happy as long as I know this in advance. It'll also help if we've agreed on a way of accommodating differing needs, e.g., I take an alternate route, with or without others, and we meet up at the end of the day. Don't forget that if there's group gear, there need to be enough duplicates among the group so that we're not all stuck traveling together just because there's only a single toolkit.
I don't know if that's helpful for you--you don't say whether you've ever done this before, traveled with these particular people, or even know them very well. Traveling in a group is difficult (sez I), and being the designated planner/leader is a lot of stress (for me). It helps if everyone feels invested and if there are backup plans (a.k.a. escape hatches) built in.
Mark
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