I'm 50 years old and have owned 3.5mm jack devices for about 40 of those years, starting with a Radio Shack pocket AM/FM radio, a good half dozen or more Walkman-style cassette players, most iPhone models, 3 iPods, and various PCs and laptops. Possibly 2 dozen devices added up.
I think I've had problems with 1-2 of the cassette Walkman devices and the headphone jacks getting static problems, but the others have been fine and never developed problems. The Walkmans mostly likely became problems because they just got used hard, jammed into pockets with stress on the jacks.
But I also wouldn't write off general improvements in construction of the jacks since then. We call it the 3.5mm jack like it hasn't changed, but over time everything about it has probably improved. Superior metallurgy means superior contacts with more durable spring force, more resistance to corrosion, engineering improvements in mounting such as tighter, closer tolerance mounting resulting in strain transferred to the housing and not the PCB.
IMHO, Bluetooth hasn't improved at all other than perhaps slightly on the audio quality side. Pairing is still a PITA, source devices are prone to wandering and shifting to other devices -- I've lost connections on my phone when the headphones in my car were still on, causing my phone to shift to my car headset despite me actively using a headset in the house.
Then there's Bluetooth's general limitations -- I've yet to see simultaneous pairing with a BT headset where you can get simultaneous mixed audio from two devices -- ie, why can't I pair my PC and phone at the same time and get audio from both in my headphones at the same time? Why do I have to fuck around disabling BT on one to shift the device to the other?