I used to love looking at the catalog and also going to Sears to check out the tools. Back then CM was the only option for me for good quality tools. I knew of nothing else besides that or the truck brands, which are realistically not an option for DIYer. However, now with the internet a whole new world is opened up. I can find brands I never heard of before and can read reviews from people that use them every day.
It is nostalgic to think about those days and how it used to be but time moves on, business models change, people's interests change, so I am not too saddened by this. I have more options today than I did years ago. I look at this like any other product. I buy majority of my stuff online: computers and accesories, TVs, books, music, even pet food. In the rare instance where I had problems I returned the items and dealt with it. The same is true with my tool purchases. I might browse the large stores to handle the tool but will most likely buy it online.
I think with cars becoming more sophisticated and more reliable that fewer young people are learning to fix them. They are too busy in their electronics and social media life to bother. To them it is not worth it, but that is ok because that's how the world progresses. Few tasks or skills carry down through generations. My dad could skin and clean animals, my grandfather could make wagon wheels with a draw knife, but I can't do any of those.
For most of us here we probably have many thousands worth of tools so the death spiral of Sears shouldn't affect us much. It's not like we were going to buy any of their massive sets or tool trays anyway.
To the poster above mentioning sewing skills, the other day I was in sewing store buying a new vacuum. My youngest daughter was fascinated by the embroidery machines and now wants to take their summer camp for kids next year. I thought that was cool. I'm still working on my son, though. He is very handy and figures things out by himself but trying to get him excited about helping and learning about car repair and woodworking.