I have Dish (so thought I'd weigh in). My brother has Direct. He's constantly trying to get me to change and I would, except Direct doesn't have my locals in HD. As soon as they do, I'll be Switching to Direct.
As far as the DVRs go, the 2 companies are similar. I prefer Dish's menu system, it's more intuitive to me. But, I don't think I'll have too much trouble updated to Direct.
I've hated Dish's customer service, I laugh every time that commercial comes on that claims they have the best customer satisfaction of any satellite/cable company. I've been with them for years, and my DVR died, I lost a lot of shows and time. They finally sent me a replacement refurbished unit, but refused to upgrade me - something I'd expect for a loyal customer. Their phone help system is full of "push 2 to be disconnected, 5 to talk to someone that doesn't know anything, 7 to shoot yourself in the head, or 9 to get to yet another menu like this one".
Despite living in a little hole, I have had very little trouble with reception. Wind, rain, clouds... all fine.
I'd check the lineup in your area for what each has or doesn't have in HD. In the East, I think it's less than a problem, but out in the boonies, the line ups are different between the two providers.