I think if I wanted to expand on Jimdandy's idea, I would simply limit the number of planes of type you could fly.
Let's say the Ta152 made it in. You get three of them, period. If you screw it up, you don't get any more til next month. You had your chance, but you didn't have the experience to handle the beast. Higher experienced pilots, or as some elitist prefer to call themselves "smarter pilots"

, would maintain a bit more caution. In short, it would allow everyone a shot at flying the elite planes, but force you to be more cautious if you wanted to keep it, rewarding the pilot who wanted to fly "realistically" (whutevah that means).
Personally, outside of H2H flyers I do not see how anyone will be expert in any of the uber planes. You simply aren't going to have them long enough to learn too much if you fly aggressively at all. The whole thing doesn't trouble me at all- it will work out somehow. I do think that saying "screw the new guy or the working stiff" is a poor attitude that some have.