I might be able to help if we work together!!
I have looked at your enclosed debug files and I can see that you haven’t done a update lately
If you go into the raspberry settings tap and scroll down to „Kernel and Package Updates and Upgrades“
next: Reboot your PI
If you haven’t installed the plugin: Remote Control do it and set it up
I need to know the status of two programs
After you have locked in with your user/password type:
sudo systemctl status shairport
look for the line „Active:“ and let me know what it says here after.
Do the same thing with:
sudo systemctl status Squeezelite
looking forward to your answer