you have to buy at least one pair of wireless headphones (and eventually they'll be bundled with phones), but you wouldn't need to replace them any more frequently than other headphones. This is the way with all changes. When wifi first became available we had to buy new modems.
As for charging them, that doesn't seem like a big pain to me. I charge my phone and laptop each day, this is just one other thing. For me the benefits -- no cables to get tangled (and have to untangle) or get caught on things -- outweigh the costs.
> I'm pretty sure that expense and complexity are inherent to wireless. No wireless connexion is going to be as cheap and reliable as an equivalent wired connexion, if only because the wireless connexion terminates in … a wire.
I hear the air pods are very reliable.
Regarding expense, if economies of scale get going, which I believe will happen, and manufacturers get more experience making them, then this will make the prices come down.