Is there a hierarchy when it comes to motorcycles? ie, In your mind, are you a more valued motorcyclist if you ride a cruiser as opposed to a sportbike?

I ride everything, so no. I've noticed most riders do thought.

If you ride a sportbike, what makes you a better rider when compared to other bikers?

I feel my experience, seat time, track time, and personal pleasure derived from the enjoyment of two wheeled motion make me a better rider moreso than WHAT I am riding.

Are there varying degrees to being a squid, or is one just a squid? ie, A squid is someone who rides recklessly without gear, however you could still wear full gear and still ride recklessly thus making you a squid?

Even I can have moments of squiddydom, but consistent stupidity and ignorance is very squid.

Are there different style sportbike riders? Some people know there are those that stunt, and those that are for show, and those that came to track race, and others to street race....are any one of these styles valued more than the other.

Leaving personal opinion out of this one.
Just look at the AMA, MotoGP, World Superbike.