I'm not sure if it's the frequency of draining or the fact that I switched from Purina One to Wellness Core with its higher quality that caused this decrease in anal gland secretions. I was told by the vet that the higher quality food doesn't reduce the production of the fluids but instead firms up the poop which then presses harder on the glands allowing a more natural release.
I like the higher quality food as well because their coats are shinier and have less dandruff. I order dog food online at PetfoodDirect with 0 tax. Just be sure to always use a coupon as that'll make up for shipping. (here's one for $5 off $30: PER5OFF)

It's no big deal for the dogs and they both get a slice of cheese after we're done.

So let's see we have to clip their nails, give them a bath, give flea and heart medicine every month, drain their glands every 2 and brush their teeth every day or so.
Who said dogs were low maintenance?

p.s. please be careful and if you're not sure about this, better to leave it to a vet or a groomer then risking injury to your dog.
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on another note, sometimes training can be challenging....