When it comes to amps, I would think that the passage of time treated tubes and SS differently. There haven't really been any new tube circuit designs in decades, though some of Bob Carver's recent work might qualify. As someone pointed out, if you were to update older tube gear, replacing aged components with new, where would the vintage gear fall short?
SS may be a different story, with newer topologies. That said, an awful lot of experimentation was done in the 70s and 80s.
Speakers have seen the greatest change, benefiting from discoveries and advancements in material science and manufacturing, as well as design and testing tools.
Pretty much everything I own is early 90s or older, except for the home theater preamp and amp, and a pair of speakers from 2008. Most of it has been recapped and restored, tube and solid state. Would love to try some new gear once I get my listening room set up. Thinking Lyngdorf with RoomPerfect might be my first foray.