In all my life I've never had a problem with wired headset not working due to driver issues. Sure there were the occasional overall sound card issues, but those were dating back to the Windows 9x days. Also, theoretically and statistically speaking, a wireless setup has more parts and more complexities, so it's more likely to fail.
There are good products where it works seemless between different devices
Citation needed. And I repeat my previous question - how exactly is one supposed to discover these set of devices? What if you say use a particular model of Thinkpad and the device wasn't tested against it? I doubt there exists a database somewhere that has list of every wireless headset tested against every Bluetooth capable device. So ultimately it's up to the luck of draw, and that's not a very good user experience. Whereas with wired, I can he 100% sure a wired headset will work if a device has the matching aux jack.
Also, the wire getting damaged isn't really a problem, any decent wired headset would have a replaceable wire, so you can always swap it out with any standard TRS/TRRS cable and you're good to go. Whereas with wireless, the battery is almost guaranteed to degrade after a few years, and it can be really hard or even impossible to replace, depending on the model.