I bought wireless headphones (for $20!) because I got tired of getting tangled up in the cable and yanking the headphones (or my phone) away when cycling, and never looked back.
Definitely the killer feature of wireless headphones I'd say. Although I bet if you used some kind of easy break magnetic connection like Apple used to have on macbooks you could get a lot of the same utility back with wired.
Not really, because I'd still have to have a wire flopping around and when it does get snagged I lose my audio. Its still not as good as just not having a wire at all.
I can pair my headphones to my laptop, start playing something, and then walk all around my house without any interruptions. I can't do that with wired headphones, I'd have to carry something around with me everywhere I go. I can walk around the room without issue. I can quickly get up and go make some food in the kitchen without interruption. I can answer the door and sign for a package. All kinds of things that don't require me to then change to a different device, restart some stream there, etc. Its just freedom to get up and move.