Another important thing, the main characters of FF8 are just teenagers. They still haven't worked out who they are themselves.

This. In my opinion, the thing that made Squall still likable and Cloud annoying was that Squall was still rational & committed to his duty whereas Cloud needed to be convinced to fight a lot of the time.

I think the part I find most interesting about all this emo discussion is most people I've met who are "emo" don't really have much of a good reason to be so depressing or disconnected.

Yeah, he didn't seem whiney to me.

Squall was raised as a child soldier, with no parental figures. He came to the conclusion that isolating yourself makes you strong and that emotion and relying upon others makes you weak.