Flying "underdog" aircraft is cool, although they are not always really underdogs.
I was one of the first online to fly the 109g2 regularly even on late-war servers. It did not seem like an underdog to me just because it had little less top speed. It ran cooler and turned better. I flew it on Sarah-Zoom server and was shooting everybody up in their stupid I-185s, La-7s etc.. and Sarah said something about it, I said I had a secret weapon, brains. I never liked her or her server and I would just go in there to shoot her and her I-185 down and then type the "sprinkles flowers" thing in the chat bar as she always did to others.
The 109f4 or f2 were always good even against late-war aircraft.
The last few years I often fly older aircraft against a late-war plane-set just because I don't think I could like myself anymore if I flew around in a 25lb spitfire or an La-7 even if everyone else had them.
Just as Dimlee pointed out, any good pilot knows they can do well in a late-war rocketship, so why not make it interesting and rewarding and jump into some older or oddball aircraft.
Knowing the opponents plane choice and flying technique can often let you pick some oddball aircraft that fits the situation and will let you get the job done.
A lot of guys like bombers. If you get to alt your gunners point out where attacks are coming from, and if you are practiced at manning a defensive gun, you can often beat up an attacking fighter so it quits or goes down.
Soon I want to put a track up of a mission I flew ten years ago in a Stuka B2. I had three BSS squad P40s and a P-39 attack me. I got the P-39 and one p-40 smoking, another P-40 crashed in a "maneuver kill", and I blew the other P-40 up with the tail gunner. Yes, they shot me to pieces but I think I could have landed except I ran out of fuel and that put me into the ground hard enough to see the aircraft explode and hand the victory to the smoking P-39, oh well....
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