Re: How do you know you've made your drum(s) sound their best?
Larry has a great point. Record your drums if you can, a lot, and do experiments to test the sound you want from 'out there'.
I really only started knowing what my drums/cymbals really sounded like once I started recording.
For example, I have an old 5 x 14 Supra snare that from my seat behind the kit really doesn't sound all that great, but out front of the kit sounds perfect, so I continue to use it.