I'd be willing to bet that the guy you responded to is not a "good Dish Network customer".
You've been on this site 2 1/2 years longer, he has only been here 6 months, and so it seems likely that he has been a customer less than a year - which means that Dish has yet to even break even on his account.
Given that he was rude to the CS rep over $5, I'm thinking it is even more appropriate that they didn't waive it.
What does being on this site have to do with being a Dish customer? I've been with Dish since 1999, but only joined this site six months ago. One thing has nothing to do with the other.