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S&H was big for my Mom too - and therefore, me and my brother. Likely got us a lot of things we needed when Dad was in grad-school. It was fun - we'd sit in the living room and put them into the booklets and then look at the catalog. Usually this meant a new electric blanket for winter or something equally useful for the time. Might very well be what got me to be a "shopper" at an early age. I think it was really good for my Mom too - something we could do and she "wasn't spending money", per se.
I know it's all relative, but I truly do miss those years. I just don't think the quality of everyday life is as fulfilling since the 'net took over everything and everyone.
I hear you as I sometimes feel there was something simpler, something more family-oriented to the pre-digital, pre internet all-the-time days. I don't have children, but my friends' families seem always on the go, much less connected and always stressed for time in a way I know we weren't when I was a kid.
I would do a similar thing as you with my grandmother as we'd "work" together to get the stamps, put them in the book and then pick what she would get - a simple, good, family time (and I was young enough that it was really exciting, when she did a "big" shop at the supermarket, to see the stamps stream out of the machine). When my girlfriend's bother's family comes over, the kids all bring their computers, etc. and spend a good chunk of the time in their own worlds. It feels much less family oriented and I feel we are all less connected for it.
That said, maybe I'm romanticizing the past a bit and, at the end of the day, I guess people want their own digital worlds more. Heck, I'm on the web doing this right now 'cause I find I connect well with so many here.