do most people have to run a cleaner down the stem and into the shank once or twice per smoke to deal with moisture, or is that considered "bad smoking"?
I'd consider it bad smoking when same cleaner-running bloke disses filters and those who use them. Otherwise, do what works for you; still, doing the cleaner trick seems like a hassle to me, but heck, I can capitalise on the habit and manufacture leather port-a-cleaners.
Again, if you're gonna puff like a choo-choo, you need to dry your tobacco, use balsa filters, or smoke straight pipes (since bents seem to accumulate more moisture at the heel than straights), or a combination of the three. You can use the cleaner if that's your cup of tea and your pipe is filterless.
Do note that aromatics don't like to be dried to 'bone dry' as they lose flavour and you'll be tasting basically nothing but burnt ash. So, drying the leaf isn't a panacea either.
I second the advice to slow down, but it's advice I myself don't really take: I have a fast cadence (one sippuff every ten seconds) which is mostly the result of trying to keep the pipe from going out (I hate constant relights because they are a leading cause of tongue burn) and the need to finish the bowl quickly, in under 35 minutes.
No, the fabled breath method doesn't work for me either.