I am not fond of "rules" as such. Leadership is about judgement. Nothing wrong with loop trails or starting a trip going downhill. In fact the latter actually may be better because your pack is heavier at the start and you become stronger as you hike more. As for loops, the leader needs to inform particpants of the plan and set the boundaries - such as we will NOT leave someone on the trail to pick up later. I would not even do this on an in-and-out trail. Once you have formed a group, you have an unwritten "contract" on the goals and individual behaviors.

The hardest part about leading a group is to get the group to see themselves as a cohesive unit, not a bunch of individuals. Those individuals who refuse to be a participating part of the group should hike solo. I make it very clear when I lead a group that their "individualism" has boundaries. They either buy into that or do not participate. It is easier to get people into this mind set on a long trip - say 2+ weeks. They really "get it" when everyone in the group ends up with an occasional "bad trail day" and need help or need the group to slow down. As a leader you can channel each persons skills into something that helps the group. For example, let a few of the hot shots go ahead at the end of the day and find a campsite that is suitable for the group. When they find the site, they then clear off all tent sites, gather water, gather wood if fires are allowed, and have everything ready for the slower ones when they arrive and are tired. On the trail, the hot shots can also carry more group gear or even carry some of the slow person's gear. Everyone then gets to go farther and faster. Hot shot stream crossers can go first and then come back and carry packs of those who are less talented at crossings. And the slow people can "pay back" these kind jestures by being up-beat, helpful, maybe cook meals, do a few more clean-up chores in camp.

Off-trail, the first person who navigates probably walks twice as many steps because they focus on the general line of direction, often having to backtrack, zig-zag around obstacles - sort of the "drunken sailor" route. The second person stays back a ways and is assigned as the "smoother outer" - his job is to refine the route, by finding the more efficient micro-path. The rest of the group then have less work to do. Route finding and navigating off-trail is mentally tiring. The stronger and more qualified need to trade off on this job.

As for those who cannot get their stuff together in time, how about a little help from others instead of waiting at your packs tapping your foot?