Sounds like you're just making it up as you go. Why do you think that group must be "tiny"? Many people have rf-only, cable or satellite connected TVs that have no idea what craigslist even is (see...I can make it up also

). My 85-year old mother is one of them, but I can come up with more than a dozen in my extended family off the top of my head. A lot of these (...again, making it up), if forced into a HD upgrade would just pick up the phone & call the cable company.
I'm sure Dish has a bunch of smart people running alternatives through spreadsheets considering how and when to proceed with transitioning from SD to HD, and they aren't making it up.
You have to realize that folks you see on the internet & on forums like this are a self-selected sample that in no way (yet) mirror the public at large.