Allow me to chime in on this thread to assist you further, @JMaassen.

Beforehand, the reason why the Customer Care Team you spoke with offered to upgrade your subscription is because QuickBooks Desktop (QBDT) 2020 software will be discontinued after May 31, 2023. This also means you won't receive critical security updates starting June 1, 2023.

In your case, we can perform troubleshooting steps. First off, please make sure your QuickBooks Desktop is up to date as well. Then, let’s utilize the Quick Fix my Program from the QuickBooks tools to fix your QBDT. Before that, you’ll want to download and install the QuickBooks Tool Hub. Here’s how:

1. Close your QuickBooks account.
2. Download the most recent version of the QuickBooks Tool Hub, then save the file somewhere you can easily spot it.
3. Open the file you downloaded (QuickBooksToolHub.exe).
4. Pay heed to the onscreen prompts to install, then agree to the terms and conditions.
5. When the installation completes, click the icon on the Windows desktop to open the tool hub.

 Then, performs the steps below to repair your QuickBooks.

1. In the QuickBooks Tools Hub, select Program Problems.
2. Click Quick Fix my Program.
3. Retry installing QuickBooks.

Let me know if you have more concerns with any QuickBooks-related matters. Stay safe!