I consider myself an old fart, but you need to get out and do more experiences yourself.
Wireless Bluetooth headsets have been pretty nice for years. Don't go too cheap (but even cheap ones can be good) but don't waste too much money either on them and you will be fine.
Pairing today is smooth and easy, never had an issue in the last 5 years at very least. Battery life is pretty good, my tw buds get a week worth of charge at my usage (and I use them for daily sport training, calls and occasional video). They get charged automatically when I put them back in the box and the box itself recharge in like 30 minutes.
And you can use them one at a time, which is good to get truly unlimited "call time". .moreover, my model can both do noise cancelation or environment sound pass-trough which is amazingly good when running on asphalt (the latter) and trying to isolate in the office (the former).
Moreover having no chord dangling getting pulled and catching around is unreliable better experience.
I had to go back to wired a few times (forgot the wireless home..) And found how much worse experience that is.
Of course, I prefer the choice and I have always purchased a phone with audio jack and will do again if at the same price/hardware level.
All my micro-usb phones have the port mangled or damaged over time. I had even to replace one, once.
All my usb-c phones have had zero issues with the port itself. And that's as well true for my kids. Once they managed to break a micro USB but they never even had a single issues in USBC.
They stand much better the forced insertion/unplugging in my experience. yMMv.