I'm new to pipe smoking, so it's entirely possible--even probable--I'm doing something I shouldn't. That said, my pipe was $20, so if it dies on me in some way, I won't be horribly heartbroken, and I'll learn from the experience for my next pipe.
I clean every other day or so, after smoking a few bowls each day. I let the pipe cool, then gently tap out the bowl for any excess ash before disassembling it and running a pipe cleaner through the shank. I dip a clean pipe cleaner in whiskey and run it over and through the bit, as well as the metal piece that fits between the bit and shank. I may have some of the terms confused; if so, please feel free to correct me, and to critique anything of mine you read.
Afterward I tamp a bowlful, toss the rest of the whiskey shot back, and relax for a clean puff. Then, I store the pipe in the cradle it came with, and give it another four to six bowls before another thorough cleaning.