I am a technician and have worked for both. Often I ask people why they are changing when I switch people from one to the other. The typical response from people direct to dish is price, and dish to direct is problems.
Purely looking from the perspective of service calls. Approximately 80% of the work I get for dish network is trouble calls. Directv is probably closer to 20% service calls. Dish network has a lot of problems with their equipment (receivers and lnbs (the eye on the dish) going out). Directv has very little equipment failure.
Dish Nework also has many fittings and things to go wrong along the way. Lets compare a basic 2 room installation. Directv: 2 fittings at the dish, 2 cables coming down, 4 fittings in and out of the ground block, 2 fittings one at each receiver. That is 10 fittings and a ground block. Dish network: 1 fitting at the dish, 2 fittings ground block, 3 fittings diplexer one, 3 fittings diplexer 2, 3 fittings separator, 3 fittings receiver, 1 fitting tv 2. That is 16 fittings, a ground block, 2 diplexers, and a separator.
Service calls for directv are typically the result of a very poor installation. A wobbly dish, and corroded fittings where a tech left them with water running strait in are 2 very common service calls.
Many people changing from direct to dish say that direct cant get the billing strait, don't know if this is dishonesty on the salesman's behalf, or they really cant get it right.
Timo, not sure whats going on there, but it is probably in your best interest not to broadcast that.
The reason you lose your HD channels 1st is that the signal is not as strong on the satellites that provide them channels. If you have a 5 lnb kaku satellite dish it is centered on the 101, then skewed to center on the 119, this lines the 5 satellites up perfectly. If it isn't centered perfectly on the 101, then skewed perfectly on the 119, (or vice-versa, centered perfect, skewed imperfect) you won't line up perfectly. The 99 and 103 satellites are small and easy to miss or get a small piece of. If you have a 3 lmb kaku dish, your mast needs to be perfectly level, and the 101 needs to be perfectly centered, because there is no 119 to base the skew off of, need to skew it at what the book tells you to skew it at for you zip code.
Skidoodoug not available yet, but I think that I've heard direct is coming out with a single receiver that will control 4 rooms. But don't quote me there.
As far as High Def Picture, some people can be overly optimistic or pessimistic. I've had people tell me after I re-peak their dish that there picture is better as well as many other claims. People think something and your not going to convince them otherwise. It is not an analog signal that is being worked with, it is a digital signal. If your the signal from the satellite is weak, it will pixilate or go out. That gets you to the receiver. From the receiver to the tv there are 2 standard methods of connecting it, component cables or an HDMI cable. HDMI is the better of the 2 for quality, but I can hardly believe that unless you have about a 240 inch screen you would notice the difference. Directv supplies component cables or HDMI cables, Dish network does not you'll have to get them on your own.(most technicians will buy HDMI cables in bulk and have them for sale if you want them.) Directv provides up to a 1080p resolution, dish provides up to 1080i, and I believe most cable companies will provide up to 1080p.
My advice to people is to switch every 2 years, both give the new customer $ saving promotions, but do little in comparison for existing customers.
I am connected to people with retail licenses is for both dish and direct, make commission for sales, willing to split commissions with customers, and probably able to install either in my area.