I have to confess that I spend most of my PoT fan time obsessing thinking about the Seigaku regulars more than the other teams' characters. So I haven't done a lot of musing on Oshitaro/Gakuto, but I may be writing a fanfic involving them soon if my schedule clears a bit, so your thoughts have been helpful to me - thanks. :)

And if you're into meta (like I am), this is a great site for Prince of Tennis:

http://intensivetennis.blogspot.com/

It's a team blog that analyzes PoT episode by episode - and hilariously, too. ;)