I don't know what the rule of thumb is for polishing one's shoes, but I know I don't do it often enough. I had a polishing party for myself the other weekend.
This revealed one key problem with owning a bunch of wingtips with perforation. The polish tends to get stuck in the little holes and along the feathered edges where the vamp and uppers meet. It takes a very thorough scrubbing to break this loose. I have tried using a toothbrush to address this with limited effect.
I will keep you posted.