I have no experience with a tail pocket or having to express anal glands. Henry doesn't gave an issue with either. He does have a sensitivity to baby wipes so I cannot use them on his face or belly. I very rarely use them to wipe his bum after a messy poo. I'm sure someone can give you some better advice. Also, I did have a dog some years ago that had to have surgery on his butt for some kind of growth, I can't remember exactly what it was, and it took him a very long time to heal. You could tell it was itchy and irritated for a very long time. I cleaned it 2 times a day for weeks even though I could tell the irritation wasn't on the outside. He eventually calmed down and stopped trying to rub his butt an everything. Good luck. I hope your baby feels better soon.