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It's not whether DISH Network or a retailer is the better choice. It's dependent on the person doing the work.

Most of the time a retailer will be the better option, preferrably one that has been in business and has been installing DISH Network systems for years. They have more knowledge/experience than the general installer for DISH directly. The good retailer can have more tricks up his sleeve, and can do some custom work if needed that DNS (DISH Network installation) most of the time won't do. DNS is more of a production output operation. They have product to put out and they are pushed by the company to have a very high completion rate which means cutting a lot of corners to put jobs in FAST. They look for the easiest and fastest way to put a system in because they are in the production business.

The retailer is completely opposite. They are not pushed by completion rate and tend to take more time on a job. The latest numbers from DNS management is that 75 - 90% of trouble calls are caused by DNS depending on the issue of the trouble call. Retailers have an extremely low count of trouble calls that they generate. That's one good reason to use a "good" retailer.

With that said, there are very good senior techs in DISH Network but the odds of getting that guy aren't very high, and many of them have moved into management - some even becoming general managers of corporate offices of DNS. Some have become retailers themselves. Michael Kelly who is the head of the customer service center and DNS use to be a retailer.

The option of whether to deal with a local retailer or DISH Network directly would be like deciding whether or not to take your car to the dealership or an independent shop for repair. There are bad retailers out there also, there might not be a really good one in some areas where people would have to resort to DISH Network directly as the best option. But an experienced installer with a good long history cannot be beat whether retailer or not.

I got mine directly from dish. I have a 522 DVR and a 322, 4 TVs total all leased. I recently ordered a 622 to upgrade to HD TV. When I ordered the 622 I ask if it mattered which of my current receivers I upgraded. I was told it did not matter as either way it was $299 for the upgrade and if I wanted to keep the 522 DVR I would just be paying an additional $5.98 DVR fee so I kept the 522 and had the 322 swapped out.
Because I needed an over the air antenna to get HD locals I went by a local Dish retailer to ask for recommendation. When talking with him about what I was doing he told me he was surprised I could keep the 522DVR because as a retailer dish would not allow him to put over 1 DVR on an account.
The guy I was talking to was the owner of the place and it was not a small store so I assume he knew what he was talking about. So maybe local retailers can not offer all the same deals that you can get dealing directly with dish.

When I started woth E*, I found a local dealer and have stayed with him though my 7+ years. I have gone through many series of receivers, I now have 921 and 622 and had 7100's, 6000, 501 and 811. I have moved twice and started with just 119, upgraded to dish 500, superdish and back (due to dma's). When he told me rumors, they usually turned out to be rumors. Things he told me as fact, have been fact. When I decided to get my 622, I walked into his showroom and walked out with it. Had it installed that afternoon and had no problem with csr reguarding changeover of equipment. After reading many of the posts here, I am very happy I went with my local installer.

For things like Dish'n'it'up (eg. 622 upgrade), you're going to have a hard time getting a local retailer to handle it - at least if you don't already have a relationship with them.

The problem is that E* doesn't pay ANYWHERE near enough to make it worth our time.