If given the choice I'd prefer now over the past. Merely because of my health issues. It was actually pretty awesome exploring early "high-speed" internet.
But for an internet perspective there's a protocol called Border Gateway Protocol (BGP) that would attempt to heal all the broken routes by rerouting through what's not broken. A bit of an oversimplification but if everything goes right the internet will continue to work.
I'd suggest looking at small embedded computers and hats for them to fit your objective.
Since you're familiar with Linux, I'm thinking an Arduino might work out. There's probably a better way but I'm imagining you configuring it to work like a USB drive and dropping in playlist files along with your music and using the hat to select your preferred playlist like a homemade iPod.
You'll want to avoid the generic junk mp3 players online since there's no way to be certain it's free of radio chips before detailed inspections. Since that stuff is typically pumped out with whatever junk was available that day.
Saw a guy who cut his finger mostly off and it was dangling. Went to the hospital with him to make sure he was ok. They couldn't save the finger. They described as trying to put a mash potato back together. 😭
It's the flying explosives that murder me.