I’ve generally gone with advances in bike technology as they’ve developed over the years. Mostly these have represented refinements in existing technology, such as the steady creep in gear numbers from 5 speed freewheels (when I was cycling to school as a teenager) through to 12 speed cassette hubs. In mechanical gears, I’ve usually been able to keep abreast of which cassette spacing would work with what combination of shifters and gear mechs.
All that began to change as we moved into combined brake/gear levers (STI from Shimano and Ergopower from Campagnolo).