[toastal]

There are ways to wrap cables so they don’t tangle. Many IEMs & hearbuds come with a carrying case like a Bluetooth pair might (without fire hazard of batteries). Wrapping up cables ‘correctly’ plus keeping them stored tightly in a container is a recipe for no tangles. If I know you are going to moving up & down often, I opt for using my pocket DAP that can support two-way Bluetooth transmission + USB DAC so I can freely move around & unplug--but more often I just replug them into my phone or DAP when doing another task, then the plug IEMs back into my laptop or audio interface when I return.

I had used a pair of wireless earbuds for a year & I can’t tell you the number of calls I had to cancel early due to listening to music earlier & now not having enough charge. I’ve also had botched firmware upgrades & an app with trackers needed to installed just to get those updates, something analog didn’t deal with. The technology is far from the total-upgrade you are pitching--especially when all your digital apparatuses have a jack, the analog convenience of pulling the plug from one to the next without the fiddling of Bluetooth menus.