Thanks to your advice, I was finally able to reproduce and solve the problem with the boombox. It had to do with the shuffle mode. So thank you!To the Dev: I've encountered a couple of bugs related to the boombox. I think it is also related to a softlock.
I've placed and used the boombox (shuffle, turned it off, relocated it). It seems, it starts itself again after a track ends. On two occasions when I used the boombox during the day, I got a softlock: After I went to bed and a sex scene was about to start (the screen is black and the text says: "Mhhhmmm....") the game did not respond to normal input. I had to load a savegame from that point on to continue playing.
Just a suggestion, but don't use LocalLow for savegames. Use Local or Roaming instead, as Windows repair functions can erase the contents of LocalLow (I experienced this once when I was repairing my profile). LocalLow is more for telemetry or log files. Files that you as a user will not really miss.
Unfortunately, I cannot reproduce the problem with the softlock during the night-time visit. Do you have any more clues? It's been a few days, but do you remember if the mouse pointer was still visible? Was the continue button visible?