Once I started using the tool lending libraries in the San Francisco East Bay, it was a game changer for simple maintenance.

• https://www.berkeleypubliclibrary.org/locations/tool-lending-library
• https://oaklandlibrary.org/otll/

Some bike shops also have public work benches with tools. https://www.boxdogbikes.com/about-1

https://c.tenor.com/gspM4OJLLi0AAAAd/tenor.gif

I was in a similar situation. Not sleep-phones, but just a particular type of headphones that I like. Have you thought about getting a Bluetooth receiver for them? It’s super annoying, but it’s the only way I’ve been able to keep my headphones. Just thought I’d suggest it if you hadn’t thought of this solution/kludge yet. https://www.fiio.com/btr3k

The other option is to get a USB-C adapter. https://us.creative.com/p/sound-blaster/sound-blaster-play-4

The horrors are naturally occurring too.