As an electronics guy the jack is rarely the issue, a TRS jack has spring contacts inside, so wear should not be an issue unless they use the shittiest of connectors or you actually damage the bonding between connector and PCB. It is 100 times more likely for the plug to fail and a 1000 times more likely for the cable to fail.
I've not seen the same failure in TRS connectors in a long time now, but I think that's mainly because few people actually use them.
Most jacks do just fine, but having the springs eventually wear out on some device or another wasn't uncommon for me 6+ years ago. Not having to worry about whether the jack is going to suck or not on a given product suits me just fine. Having it attached to an adapter means I can easily swap it out if it wears.
That said, some of the sibling comments are reporting wear on USB-C receptacles when used while running... The mechanical design of the Apple Lightning connector seems to me like it'd be more durable, since it's tapered and doesn't have that center alignment thing. But maybe the contact springs of Lightning wear out faster as a result? I haven't seen any data on this, just speculating.
I ended up buying a small battery-powered Bluetooth-to-3.5mm receiver that I keep in my left pocket, and then send Bluetooth audio to it from my phone in my right pocket. It's a pretty ridiculous setup.
I've had the area around jacks get scratched over the years, but I've never had them fail due to mechanical wear. Is this common for others?
I've certainly had the micro and mini USB ports fail on me over the years though.
MiniUSB was a busted connector design from the start, which is why the industry moved to Micro USB so quickly. Many MiniUSB receptacles in the wild were failing after thousands or even hundreds(!) of insertions.
Not a problem (like, never) once I switched to Apple… but then they removed the jacks.
But as others have mentioned, I too have had quite a few Micro-USB and USB-C connectors fail over the years. But almost never the trusty old and dearly missed minijack.
Headphone jacks were a major wear item on older smartphones, and waterproofing them is very annoying as well, requiring a ton of adhesives. I had to take the back glass off my old Xperia Z2C three times over its life to replace the headphone jack, and the waterproofing was totally shot after doing so. At the end of the day, I honestly don’t mind the trade off, although I can see how it can be annoying for others.