I prefer wired ones, mostly playing devil’s advocate here.
Every pair of cheaper earphones or earbuds I’ve had fail have failed due to the cable.
We switched my oldest to a pair of BT headphones because he seems incapable of keeping track of the cord. It gets caught, he pulls, and something has to give. Longest lasting set he had in 2025 was BT.
Going cheap is the problem here, good earbuds and headphones have replaceable cables.
I'm the same way as your oldest, if I'm up and moving around while wearing earbuds/IEMs I run the cable through my shirt.
Expensive headphones have much higher quality cables...
Same. Either the jack fails or the one of the buds stops working or the cable on one side of the buds gets cut somehow.