I think Red Baron is probably the best of the flight sim career modes; although EAW had some great ideas in it.
I agree that IL-2 has always been a bit cold as an off line game. Some of the hand built missions/campaigns are wonderful, and can do a surprisingly good job of historical "tuition"; but the replayablility of anything scripted is limited.
The inbuilt campaign generator wasn't bad when the game was new, but these days it's an insult for a new purchaser to find out he's paid for a game wherein so much of the content is unavailable to a new user (Spit or Temp or He 162 campaigns for example).
BOB2 had fantastic promise, but was so flawed at launch it never really recovered. I think it was the only sim ever made where joystick button assignments were hard coded, despite the in box literature showing a programmable MS sidewinder!
Much of what keeps IL-2 running comes from the EAW world, such as Hyperlobby and DCG.
It'll be interesting to see if SOW will be sophisticated enough to stand alone or if it'll still need support from the EAW legacy.
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