FYI regarding musician wireless packs, they do use radio frequencies but not Bluetooth. Shure just came out with their PGX-D digital wireless systems in the last few years. Basically it allows the system to disregard any analog signal which allows them to get a cleaner transmission. It also operates in the 900mhz range whereas Bluetooth operates in the crowded 2.4Ghz range.Continuing your guitar analogy, then you see that band in concert and they're all wearing Shure body packs.
I have both wired and wireless headphones. My Bluetooth headphones are both quality products but yes I occasionally experience a click or pop, that's very rare. I'll replace my wired headphones with lightning cable equipped units, I accept that technology advances and I move with it but if I weren't willing (or able) I'd be comfortable with the adapter it will likely ship with.
I can understand the possible inconvenience of wanting to charge while listening but do you really never take your headphones off? The iPhone 6s is rated for 50 to 80 hours of audio playback (depending on whether you have the plus or not). In that time are you never going to sleep or go to the bathroom or go to work or shower or anything else that would have you remove your headphones and put the phone on a charger? Maybe if you use headphones for 10+ hour long movie marathons but even then that has to be an extreme use case. Eventually you can put the device down long enough to recharge without using your headphones.
If you are busy synching to iTunes you can also just play your music back from iTunes while you synch (it can do both, I do so frequently).
It's clear a lot of people have concerns about this move but I think we'll find reality doesn't have any significant impact for 99.9% of users (and that's probably being generous).
Also, I think you underestimate the distaste some of us have for having another thing to charge. I would love it if I never had to charge my phone, and now I'm supposed to charge my headphones everyday too? Hairy no.