Having the fastest rider with the patience and discipline to ride slower to stay with the other members of the team is probably a good starting point.

Fleches aren't that difficult, and doing 360km in 24 hours is achievable by most riders who have done at least a 200.

I think the two keys are for the team members to be tolerant of each other's weaknesses, and to try to ride through the night until you get to a point where you have time and distance in the bank, and so you can nap a couple of hours, then ride the remaining required distance in the last hour without any qualms.

An easier course is probably desirable if you have inexperienced riders on board... but does that mean having fewer hills? Maybe not.

The Fleche Opperman I did two years ago was a blast, although we had a little bit of support along the way which helped. We finished with around 383km for the 24 hours, and that included a two-hour naptime break during the early morning darkness.