Hi elixirEU,
Welcome to Apple Support Communities. I understand you're unable to update to macOS Catalina as you continue to see "Upgrade Now." I'll be happy to help and point you in the right direction.
If you haven't tried yet, I recommend to start up your Mac in safe mode. You can review the benefits and details of how to start up your Mac in safe mode through this helpful article: Use safe mode to isolate issues with your Mac Once that's done, you can then restart your Mac normally and attempt the update for macOS Catalina. In addition, please be sure you have enough available storage space for the update. Here's how: How to free up storage space on your Mac
For any reason you continue to experience the same behavior, I suggest creating another user account on your Mac and attempt to update the software. If needed, here's how to create a user account on your Mac: How to test an issue in another user account on your Mac
Cheers!