FWIW I've exclusively used wireless buds and over-ears for years now and none of those things has ever been an issue for me.

For charging, I take five seconds at the end of the day to check the charge and plug them in overnight if necessary. I've never once had to think about wireless protocols. I've had to re-pair them a literal handful of times. I've never had to use a dedicated app.

Are there trade-offs? Yes, absolutely. But for me, none of them come close to rivalling the massive inconvenience of having your head physically tethered to another device. Being freed from the cord outweighs every other consideration by an order of magnitude.