I've been using a single bluetooth headset on numerous devices for a while now and it works great for me. I've got it set *not* to automatically pair with a device. When I want to connect to a device, I connect to it from the bluetooth menu on the device when I want to use it. It takes about the same time as untangling and connecting a cable. If the battery starts to die, I connect a USB charging cable.
Personally, I couldn't stand being tethered to a device with wires connected to my head. The cables constantly got tangled and prevented my own mobility. I tried longer cables and I destroyed them by rolling over them with my chair. Also, I had to replace my headphones at a rate of at least 1/year. The problem every time was cable-related. I tried expensive headphones and cheap headphones. Same result- dead within a year (and, yes, I take care of my stuff).
With the exception of audiophiles and heavy users, I think this whole headphone jack thing is a non-issue. Keeping the device charged is the biggest issue but "charging my stuff" is just part of my daily routine now (I make sure I charge my phone, watch, headphones, laptop and tablet daily). I haven't had many battery issues for a while now. If you use your device a lot you have a legitimate gripe, but otherwise bluetooth does work and it does have advantages.