I didn't mind the pity badges for the time period. I feel they served the purpose of giving depth to Ash's character. I also feel that they were to show his inexperience, and act as way of teaching Ash life lessons. And like some have said, most of the pity badges that were given were done so because of unfair obstacles in Ash's way or to give a character choice context. (Brock following Ash, Erica denying him gym access, Sabrina being impossible to defeat, etc.)
But that being said, I think it's a writing mechanic that won't work anymore. While Ash is still not a champion, he's beyond the point where a pity badge is acceptable. He's a skilled battler (despite making rookie mistakes from time to time) and it's even been written into his character over the past few generations that he doesn't like receiving badges he feels he hasn't earned. Again, was good for the time it was used, but I don't think pity badges will be making a comeback.
