Your focus on "dweeb" is where you split away from what I was talking about.
I'm not making qualifications like "dweeb" or "elite" -- they have totally subjective connotations.
I'm talking skill and capability, "relatively objective" things (far more objective than "dweeb" and its loaded meaning) that would play a big hand in the outcome of a fight.
The pilot of an I-16 can determine the outcome of a fight, but sometimes the nimbleness of his ride determines what the pilot can and cannot do. Fly a Fw190 like an I-16, and no matter how good a pilot you are you won't turn any tighter than the plane's wing shape and weight will allow. You can't make a silk purse from a sow's ear.
This.
EZ Planes:
Spits, N1Ks, P51Ds, Typhoons, HurriC, Zero
Non-EZ Planes (Yet still LW competitive):
P38s, 109s, 190s (Fighting in them), C205, Mosquito, Yaks
I figured I'd make the official list so there is no confusion.

@ Ez Moders
Make no mistake, just because you fly an easy plane does not make you any less skilled. Inversely, flying a Non-EZ plane does not make you any more skilled (Ahem, FlyinFin).