for gate or wormhole jumps, a scout always goes first, can cloak up and burn MWD in a direction, and then warp the next 9 in sequence a few seconds apart to facilitate the burning and cloaking of all the ships. will take some extra time, but if you needed to, it could be done.

Also, if you are in Kspace, and there are no neuts in system, no need to worry about it. you can activate cloak in warp, right? you could just hit their warp hotkeys in a round robin, and then activate cloaks on your way to desto... still slower and a LOT more micro than normal, but safe.