I think that as long as the engine has the rights "hooks" built into it from the get go, you can go as far as you like thanks to the built-in modding support.
Oleg Maddox said that it's already possible to create some sort of dynamic campaign with the stock game, but according to Luthier they wanted to do more complicated stuff. I guess we'll have some the appropriate data output and log files, so that for example a programmer can script some kind of plug-in (let's not forget we'll be getting an SDK some time after release) that tracks mission results from one sortie to the next and acts accordingly within certain parameters.
As far as what the future holds, brace yourself because i'm going to go wild and get too much ahead of things.
I guess it could be a "be an ordinary pilot following orders" deal, all the way to "manage every single sortie" if the rights community mods are available.
However, imagine now having some of this functionality online, with people being able to plan a mission within the server lobby, invite people into it and suddenly the game automatically assigns you a common radio frequency, call signs to use with the ground controllers and gives everyone in your flight the waypoints and flightplan on the in-game map: it's like a fusion/combination of DF server, coop and single player.
Add the ability to schedule AI flights that you can then hop into and take control of and you got the means to recreate real raids on real size maps, with whatever tactical considerations that means affecting the mission towards a more realistic, once again, outcome.
If i can schedule a group of AI B-17s to take off and start heading for a target in the Ruhr or do the same for a bunch of Ju-88Cs patrolling over the bay of Biscay and then take control of them 3-4 hours later, i will be able to fly the interesting parts of the mission while facing as much of the real considerations these guys faced.
And the main thing here is fuel loads and the fear of not making it back to base in case of damage, because what we currently have in IL2 is aircraft with a few thousand miles of range flying sorties of maybe 200-300km round trips at most and usually within gliding distance of a friendly base, all the while loaded with merely 30% fuel with whatever non-historical advantages that brings in combat
I also think dynamic campaigns work very well if they include scripted missions of selected historical events. This was done with GWX (grey wolves expansion) which is a mod for the silent hunter 3 U-boat sim.
Ship traffic was very much dynamic, but selected operations that were well known actions had been scripted to occur in the campaign regardless of other factors: if you were around Narvik during the invasion of Norway you could see the German battleships and the royal navy duking it out along with the transports moving troops, if you were silly enough to brave crossing the channel during June '44 you could easily stumble upon the D-Day invasion fleet (in fact a guy posted screenshots of just that a few years ago on subsim.com from his hydrophone station and there were contacts everywhere), things like that.
Personally, i would fly as just a pilot and wouldn't probably manage the strategic aspect if such an option was ever available, however i'm not against it because it has a certain functionality and set of needed tools that could carry over very well to the new multiplayer mini-campaign mode.
Maybe 2-3 years down the line i'll be able to join a server, click on the map and see a breakdown of the campaign objectives or even data at the strategic level (amount of aircraft
per type, ammunition , pilots/team "lives", fuel and their respective rate of replenishment for example) to decide what to do. Then i could click on an enemy installation and select "last known intel", it would display the date of last known data along with "installation capacity %" and "estimated production output" for factories, or "estimated aircraft stationed" for airbases, things like that.
Then i'd select a mosquito, click on the "flight planner" tool and draw up a flightplan for my next mission. My AI navigator would provide course data to help my fly it, i'd go over the target and snap some pictures. If i made it back to base i'd be treated to some black and white screenshots and an update to the campaign map's intel on the specific target. Other people could then use this to do similar stuff and plan air raids against the target, escort for the bombers and so on.
Such a thing would be awesome for a very simple reason: it would give people of varying tastes an incentive and a way to all fly together in the same environment. The wacky folks like me would be flying anti-submarine/anti-shipping patrols and recon flights, the fighter guys would always have something going to intercept, friendly bombers to escort and targets across the channel to raid and flying as a bomber guy would give some very tangible rewards.
And the best part of it is that as long as the engine is moddable by design, it's not the developers who will have to do it all by themselves but hobbyists from the community will be able to help.
Most probably i'd let the folks who enjoy the strategic aspect do most of that, what i would do however is browse a list of sticky messages they had posted on the team lobby with the kind of missions they want: "recon needed at target X", "top cover escort requested for bombers, contact me for details" and so on, then i'd plan my mission, invite my buddies to my flight and go out to do it.
I think it would be great because it would allow everyone to become as much involved as they wanted with the deeper aspects of air warfare planning, or not at all involved and keep flying missions that other people provide (like it is today on mission based DF servers) or even ad-hoc sorties of their own if they just wanted to have some quick fun.
Is it going to happen tomorrow? Definitely not. But i can see it making its first steps within the next 2-3 years