Going to be changing my jetting over the winter..
 

I haven't rejetted yet since installing my Two Bros cans. My question is, should I do anything else first? Like lose the airbox in favor of some K&N's or something? I was thinking that also might be something I would want to do down the line, and no sense changing the jetting twice... What would you suggest>?

Ok then, what about if I just compensate for the cans? One or two up in the front and rear? Maybe some adjustment to the needle height?

If your going to install a K&N I suggest you do that first. Then adjust the carbs from there. The K&N should flow more air so you should set up the carbs for that.