1) Before I couldn't take it anymore, my DVR would crash while on vacation, so I would miss several of my shows. I would do the power cycle trick, and then it would work for a short time. When I told them I wanted a new box because this one wasn't reliable, they refused on the grounds that it wasn't broken at that moment. My entreaties that waiting until I got back from vacation to find out that it has broken again went on deaf ears, as I spent an hour escalating the issue, finally telling them that if they didn't send me another box, I was going to cancel the service and fight the "early termination fees," as they had not provided the service they'd promised. They did finally send me a new DVR, warning me about charges if I didn't send the bad one back. Like I'd want to keep it.
2) A few months after this, I discovered my bill has gone up significantly. After some time on the phone, I found out that my account had been crammed. Without my permission (or knowledge), they'd signed me up for "Premium Channels," with a teaser period, which had expired. After the third time they used the scripted line "So you want to cancel the HBO, Starz, and Showtime you've been enjoying for the last three months," I reminded her that I had NOT enjoyed them, as I had not ordered them, nor even known they were there. They eventually removed them and reversed the charges.
3) When travelling, I frequently would use up the maximum consecutive connections, only to discover that one of my shows would have been pre-empted by a house ad from Dish trying to sell me some new channel or pay-per-view movie, so I would have missed one of my shows, and there was nothing they could do about it.
4) Seven years ago, I switched primary residences. Since I was no longer going to be at this location often, I went with a lower-cost package from the phone company (which I had avoided when I'd lived here full-time, because I didn't want a single point of failure for my entertainment). When I called Dish to cancel, they wanted me to climb the roof and retrieve their Standard-def dish for them. I informed them that I park in the blue zones and it was ridiculous for them to expect a handicapped person to climb up on the roof, but I would make the house available for them to send someone out to retrieve it. It's still there, and will probably stay there until the next time I re-roof the place.
The new place has had DirecTV, and in the last seven years I have not had a problem.