This is a big new system that I wish to implement. A really really huge one that will involve many many commits, so I'm trying out the milestone system instead of just issues. It will involve many issue-todo list things.

Make a system so that the general can send out a runner with orders to others. So for instance, order 5 militia who are out somewhere to go to a barracks (specified location) and train to become two-handed swordsman, or to come back to the general, or to go to a specific location and attack.
Or, send out an order to a bunch of houses to produce more villagers. Or order a bunch of citizens out gathering lumber somewhere to go and mine gold somewhere else instead. Or send out a man to a research facility with orders to research whatever. Or tell some men to go and garrison a tower. It has to be a very robust system.

Also, when giving the orders, one does not know that the units/buildings involved will exist. Maybe the enemy came and killed them. Make sure that the behavior in this instance is well-defined. And make it variable. So you can say, give this order to 5 swordsmen, but if any are dead, or if more than x are dead, don't give the order and return to me with that news.

Also, make it possible to order something like the following. You ten swordsmen go garrison this castle, with a house and barracks nearby, and if any of you are killed, tell the house to train another villager, who will go to the barracks and become a swordsman, and join you, continuing until there are ten of you again.

Also the order: periodically send out a x man scouting group along this patrol route. Do it every y seconds/minutes. Maybe that patrol route will involve reporting back to the general and giving him information about how everything is going, a full generic report.

Basically, you ought to be able to order almost anything that you could just say directly when the units are present near the general.