Dauntless: I posted some ideas on orders a while back (here) that seem similar to what you are suggesting. I hadnt thought of the initiative thing, but it had occurred to me that a stealth option may be useful. Stealthy units would obviously take longer to reach their target but would stand a good chance of catching him unawares. I am a little concerned about the complexity of the UI though.

As for units, my basic thinking is that units are automatically formed into squads - the player never has to piddle around with individual soldiers, but just issues a command to a squad of say, 5 soldiers, or 3 tanks or whatever. This is the smallest unit the player gets to control. What about larger groupings? (eg platoons/divisions/companies) It would be nice to group say 30 different units into a single platoon, and give the platoon orders - these orders would form a kind of overall objective - and then give individual units separate orders, on completion of which they could return to the main objective. Thus the player could be reasonably sure that even if his units are being ignored, the chances are they are doing something useful...