Understanding "Ore"

Recently we subscribed to TV Japan at my house so that I can try to keep up with my Japanese a little better (or combat the inevitable decline a little better, anyway). I don't watch TV a whole lot, but now when I do, I try to get a little J-語 in. Probably watch a lot more Japanese TV now than when I was living over there, ironically.

Anyway, a while ago I had this kids show on and had a realization about the use of the first person pronoun, which I've talked about in the past. I realized that I still don't completely get it, and I don't know if I ever will.

I refer to myself as 僕 (boku) in most circumstances, unless I'm trying to be especially polite or respectful. This strikes me as kind of a softer and maybe a little more...I dunno, sensitive (?) way of saying "I" or "me." I think doctors and professors and guys like that might be more likely to use 僕.

On the other hand you have 俺 (ore), which is the pronoun of choice for all your tough guys and your dudes who are trying to sound masculine. Despite being the more "masculine" of the two (Yoshie once called me 男らしい) for using it, I've also been told that lots of guys start using it when they're little boys. In other words, there are plenty of males who use it when they aren't that tough or masculine but just want to come across as such.

Oh yes, the kids show. So I was watching this show with a bunch of people dressed up like animal mascots, and noticed that the cow (who has the voice of a little boy) kept referring to himself as 俺 (ore).

Pretty dang far from badass.

So while I understand the basic feeling of each of these pronouns, I think there's still a lot of nuance that's escaping me. Maybe one day?