I'm from 1990, so not much old tech for me since I work, the first official record I did was in a korg portastudio (not the best quality for today standards, or even at the time, but a practical all in one tool)
I worked with in the box quite a lot, but I also had the chance to use a few times older tech, and I can say I did enjoyed working with it and also that I did learned a lot. Would I choose it for a production? I really don't think so. Would I like to repeat the experience given the right conditions? I really think so.
The newer tools provide a lot of things, but you can't forget there's a lot more into it than the technical specs to it. I've found quite often older tech killing the newer one, we are quite far away from guitar players to stop using stomp boxes for instance. Still a digital pedalboard is much more compact, flexible, etc. If the art demands for it, is not the tech specs who decide if it's right or wrong, is probably the satisfaction with the final product, at least from the money guy, for the lack of a better decision maker.
JS