I think it depends on who is in the photos. I have friends who post photos with me in them, and while I'm not thrilled as I am very private, i will untag myself from them. I am very private, and am not comfortable with my friend's 300+ friends being able to view me in pictures...but that's the way it is. So I have no problems posting photos with those friends in them, as I know they are not as fussy about it as I am.
I did however post some older photos of family, and friends, from HS - but I only allowed those in the photos to view them. I know they won't care if their brothers or sisters see them way back when, but wasn't sure if they'd be comfortable with everyone I know viewing them.