You have an issue here in that you havent determined the nature of the fight.
I figured we were trying to use our five planes to maximize our coverage across the board for all possible missions. Each nation had to play the hand they were dealt, and therefore came up with different planes for different missions. Not knowing what to expect, I wanted to get every mission taken care of, and I think that I did a fair job of it given the 5 plane limit.
Interestingly enough, my favorite planes didn't make the cut. There just isn't room for a Yak unless you are totally devoted to ground support (and covering that ground support). Instead of Il-2s, I'm stuck with Jugs, which wouldn't need the Yaks nearly as much. And I don't have a true CV strike capability, though with 2k of bombs the Hog does a fair job with it. And really, how can you bet against the 109 series as an interceptor? Max Climb, good high alt performance, gun package from hell. The main limitation of range is minimized by the nature of the mission.
It's a fun exercize. How about it we limited it to aircraft in game and available in 1941? That would change things quite a bit I suppose.
-Sik