Good post.

The "envelope"- order seems good. It is possible to do this in the game, but it requires some micromanagement, and is therefore not worth it a lot of the time.

Also I like the suggestion to delegate command of a group to a Captain/ Leutenant- character. In MTW, each unit already has a named leader; it would be good if these characters could be given AI, and a personality that you as General and factionleader had to take into account.