Bear in mind that you’re talking to a guy who, when he did a super bug mod for FP/ArmA, added in a buddy pod and in-flight refueling capability in a game where the map area is typically smaller than 30x30km. 
You may/may not have played Longbow 2 back in the 90s, but I think the format it had was a bit similar to what you’re getting at. IE, it had the whole works of weather, commanders intent, etc. all in a opord format, with a clear objective for each flight in a given mission (recon, strike, escort, and so on). Granted, in that environment there were no refueling assets, AWACS, and so on, but in this context it’s just another part of the puzzle that can be put out there for our own uses.
My take is that DCS is rather weak in the briefing phase and debriefing phase and it would be nice if we could get more improvements there – especially at the debrief. The briefing doesn’t give a lot of room for a lot of the necessary briefing text and the big honking huge images on the left side tend to hog what should be a verbose description of the mission at hand. Actually putting together the mission is relatively easy in this context, especially if we keep the focus on what the player(s) mission(s) are. As you’re well aware, the strategic goal at the top is what determines what happens under the hood, and in the context of what a lot of us do in DCS doesn’t even touch upon that. Yeah, a lot of that would be considered filler, but if we’re going for realism, it’s an essential part of what is happening and why it is happening, coupled with what the intended end result is going to be.
What I can imagine is that, in the EECH/AH and LB2 formats, is that unless players are present, AI will take over all the tasks of a particular mission. In the presence of players, roles are available for a given mission and they take over the flight. I’m not sure how things work in the fixed wing world, but rotary wing tends to favor 2 ship over larger formations, so that’s what I tend to aim for when I build scenarios. For example, a test scenario I made had 4 Su-25Ts separated into two flights, one tasked with DEAD, the other with SEAD. A flight of AV-8Bs backed them up as an additional layer of SEAD, while a pair of F/A-18Cs provided escort from enemy fighters. A 4 ship of M2ks served as a fighter sweep, where their goal was to keep enemy Su-27s from intercepting the attackers. An E-2 provided AWACS while a S-3B was available for tanker support, though naturally they only served the M2ks, AV8s, and bugs. Now, inside of all this there was no real briefing or any background material, as it really wasn’t much more than a learning experience for trying out some stuff in the mission editor.
Anyways, rambling on and on, but if we can get some idea of what the real world system works like, we can put together missions more in tune with what we might expect if we were operating from that level. Much of this is based on my lack of what really goes on (as the last time I played multiplayer was FC1.0 in '08), so I don’t even know if anyone has tried anything like that. I did play a few missions/campaigns like that in the context of IL2, but that was a very different environment altogether.