I've had ridiculous amounts of aircraft present at the same time in one mission back when i was still flying European Air War. That game is older than IL2 and it could do 255 aircraft on screen at once without problems. Of course, it wasn't as detailed as IL2.
However, despite the fact that graphics, FM and DM were inferior, it was superior in the amount of random events during missions (returning from an escort mission you could stop time compression/autopilot and fly manually and you'd find convoys to strafe), the way you commanded the AI (and they actually listened and executed) and the amount of aircraft in the air.
I'll be very excited if we can have something similar with SoW quality FM/FM and graphics, because it adds tons of immersion. In that mission, i had 12 FW190s under my command and going up against 36 heavy bombers and 12-24 escorts. Instead of engaging i sat back and radioed for reinforcements twice and lucky me, i got them both times (this didn't happen all the time, sometimes you didn't even get one flight). So, we were now 3 flights of 12 on the LW side (36 planes), against 36 bombers and 2 flights of 12 escorts (36 heavies+24 escorts=60 total USAAF). This was a grand total of 96 aircraft. The thing is, there was a second group of 36 bombers a couple of miles behind the first one.
FM/DM and graphics aside, just seeing 132 aircraft going at it in a small part of the sky, following realistic tactics (ie only the inexperienced enemy AI escorts gave chase to the deck, the rest would just try to spoil your attack runs and stuck with covering the bombers like they should, and you could see top, close and lead cover for each bomber group) and watching flak puffing all around kind of hammers the point home in a very effective manner.
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