My retro grouchiness spans several hobbies and pursuits. I make furniture with hand planes and chisels. I still make photographs with a medium format Rolleiflex camera and film that I hand process (as well as a Fuji digital camera that I can use the same way as my 40 year old Nikon SLR—and with the same lenses). I've never stopped to analyze why I'm a little stuck on old tech, but... let's see:
1. Cost. I can afford the very best obsolete technology!
2. Process. Older tech keeps you closer to the mechanics of the process, which I find interesting and rewarding.
3. Engineering. The feel of a Rolleiflex from 1956 versus ANYTHING manufactured in 2018? I'm not sure a camera like that could actually be made any more, and if it did I can't imagine how much it would cost. The last batch of Rolleiflexes were very expensive and they lacked many of the subtle mechanical aspects of their ancestors. In hand tools and bikes you can still get boutique versions of what used to be more commonplace manufacturing.
I guess I'm someone who appreciates a little texture, resistance, learning curve, etc. I don't value easy and convenient for their own sake. I did ride a modern road bike for the first time a couple of weeks ago while on vacation and it was fine. But it wasn't some kind of crazy revelation versus the 35 year old bike in my garage.