I think the last big jumps would've been give or take 2010 with LED Technology making bike lights so much less power hungry and brighter and obviously battery technology that gives you the e-bike

Since then, it's been general improvements in material technology and attention-to-detail rather than anything particularly ground-breaking.

The attention-to-detail aspect of device design is so important. A lot of aspects of the design of bikes could have been implemented 100 years ago, but it simply took a long time to try out lots of different permutations and figure out the best way to do things. Things like thru-axles, or universal derailuer hangers. Bikes from the 80s are totally rideable (I use one as a city bike), but they're definately mechanically quirky and annoying compared to something even a decade newer.

There are a lot of devices and mechanism out there that would benefit from the nit-picky development that bikes have received over the decades. It's distressing when you see modern versions of a device that have somehow regressed.

Not 150 miles each

Imagine 150mi on a penny farthing lol

funnily enough for roadbikes this is proven to be better, but the UCI - basically the global regulation body for road cycling - banned it fearing it'd lead to loss of spectators on account of looking like shit. in fact anything downtubeless is out.

To be fair, I agree. Triathlons are not regulated by the UCI and as such triathletes ride something like this aesthetic nightmare:

At least they get pissed on, I guess

Similar trajectory to firearms honestly.