I have this wonderful idea to sortie a task force and have the player follow it, as an escort. The patrol orders will give you the time the task force will arrive at certain checkpoints (think the waypoint system when moving from Lorient to your new port in the far east in Operation Monsun) give the base course and speed of the task force at this given waypoint and let that be that, the player can (and probably will) follow the task force, breaking off to engage a single merchant or something.
However this cruiser idea leaves a lot of possibilities open. it will be impossible to set up a complicated task force with search patterns and formations but if the friendly ships come follow you in a column, we can make a truly accurate (and, historically brutal) Channel Dash!