I'm sorry to hear of your issues with Buddy's tail pocket. But I'm glad to hear that he should be recovering soon and not have to deal with the infections anymore. I'm sure that will remove a lot of stress from your life as well as Buddy's.
My last Bulldog, Bruno, had a horrible tail pocket. But there was no "extra skin" around his tail. His tail actually corkscrewed from the base back into his body and then came back outward at the tip. So it was tightly pressed into his hind end. It's kind of hard to describe and I've never seen another Bulldog with a tail like his. He kept getting infections and his vet was to a point where she was ready to remove his tail if that particular infection didn't go away and stay away. Luckily I was able to get rid of it and keep it gone. At least once per week I used baby wipes over the tip of my finger to wipe out the brownish paste that would build up in the pocket and then I would use cotton balls to dry the pocket of the moisture from the baby wipes. Then I put a medicated powder into the pocket to help keep it dry. The only way I could get him to let me do this was to put him up onto a countertop or a table. Otherwise he hated his tail being touched. Thinking back about this he was a very trusting dog to let me mess with his tail like he did.
Anyhow, I'm glad to hear your Buddy is on the healing mend!