he has way too much entitlement and way too little self-awareness to be "cool." He's the guy who wears khakis and a dress shirt to school every day because he thinks it impresses the adults. That's Cyclops.

You're right on this but I think it's an indication of how poorly the writers have dealt with the character.

Scott isn't supposed to be the entitled douchebag. He's watched his parents die. He protected his brother as they fell to the earth then his powers develop and he's blinded to keep from destroying anything and anyone he looks at.

He should be emotionally damaged, a hardass like a few other orphan-heroes we all know and love. Being found by Xavier would be a miracle but then he meets Jean, the love of his life. Then Xavier dies (X-Men 42, 1968) but doesn't. Then Jean turns into a goddess (X-Men 101) then turns evil and then dies (the classic X-Men 137).

And then we get into Madeline Pryor and Cable... honestly, Scott should be a basket case. He's had his parents, father-figure, girlfriend, and wife all killed right in front of him before the age of 30.

He's had everything taken away from him, some things multiple times. How could he possibly be an entitled douchebag with a history like that except through exceptionally bad writing?

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Another theory: the reason Scott doesn't make sense is Xavier. He adopts these kids in their late teens, trains them as a small militia force and sends them up against terrorists (Magneto and the Brotherhood), thugs (Unus and the Juggernaut), and government agencies (Trask).

Xavier would be giving these kids the occasional psychic nudge to keep them from sliding into a psychological break or developing PTSD. I'm sure after Jean died (the first time), Charles sat Scott down and scrubbed his mind so he could keep his favourite soldier on his feet.