Sorry it turned out so bad for you but I have had no problem changing over to HD and when my parents moved and upgraded everything went smooth for him as well.
You may not think that HD is a big deal but if it isn't why are you making such a fuss about it. I love having my programming in HD as does my roommate and my parents. I am nowhere near being called rich but when I got in my new house my roommate and I decided we wanted to go HD because we are technology geeks and figured if we have such nice TV's why not watch the best programming we can. As for your comment about more money then brains I think I would have to disagree since both my roommate and I have Bach. degrees, I am going for my masters and he will have his Masters in Electrical Engineering in a little over a month. To you it may not be a big deal but after a long week at work I like to relax and watch my favorite shows in the highest quality video available.