Oh no this is all too relatable. I groaned at the RTC Connecting. Just pure dread. An excellent psychological horror experience.
For real, I love this, really creative way of recreating Discord and Windows in Pico-8 and a cute story - I think a full game going down the rabbit-hole of technical difficulties would be amazing, like having to go to Google and typing in the issue you are having and trying fixes!
Great work!