I think you're right that the word connoisseurship is generational. It's been replaced with "geek" which is fair. It has also been democratized because now you can be a wine geek or an opera geek. Geek is no longer an insulting term. A geek is just somebody who knows something about something. A dork is still an insulting term and usually it's earned since dorks are almost always rude and mean as well awkward.

I feel like a central concept of connoisseurship is being amateur, in the non-pejorative sense.

I used time to explain connoisseurship to financial people when I temped in their offices by saying it was the difference between investing and trading.