I'm not worried much about the boxes. I've had a DVR from Time Warner since they first came out with them (before that a standalone Series 1 TiVo that I still use), and honestly they shouldn't have even called them a DVR until maybe last year. The reliability was horrible, but that's been fixed. Now they just need to work on adding features and making the interface easier to live with. I switched mainly because of the two tuner capability, and HD capability of the TW DVR, but when I gave up TiVo it felt like I went from Mac OS X to DOS.
My hangups with Dish right now include the upfront cost (I had none with Cable, even with a HD DVR), the lack of interactive features (such as On Demand), the cost of the boxes (I can still choose rather or not I want a box on all my TVs with cable), and the overall cost of the programming. Right now I get all the movie channels, all the HD channels, all the regular channels, the HD DVR, a SD box, and all the Premium On Demand channels for right around $105. Now unless I'm missing something, Dish can't touch that price, and I really can't justify the upfront cost, plus the increase of the monthly cost, just for 17 more HD Channels, especially when Time Warner is supposedly adding more HD channels including locals in my area soon. I thought maybe I could get more for less with Dish when I made this post, but after reading things here, and researching, it doesn't look like it'll happen.
As far as reliability, I've had two outages with Time Warner that I can remember. One involved the Ice Storm in 1998 when I was without power and cable for a month, and the other was just recently when some drunk took telephone pole out. It's been rock solid. More than I can say for my DirecTV dish at my camp (which to be fair was a bad installation that the installer refused to fix), which went out if you sneezed. I know that with a proper installation a Dish can be just as reliable, so that's not a problem really.
Anyway, thanks for the information, I may still switch in the future.