I appreciate all the details you've provided to be able to track vendor insurance, EStier.

General Liability and Workers Compensation Insurance and the option to set an automatic alert on these fields are available in QuickBooks Desktop Premier Contractor Edition. You'll want to upgrade to be able to use these options and have a way to track vendor insurance. 

Let me show you another way on how to upgrade your company file. 

1. You'll want to save and close all windows.
2. From the Edit menu, click Preferences.
3. Click General in the left menu and then My Preferences.
4. Check the Bring back all one time messages and then OK.
5. Close and then reopen QuickBooks. You’ll now have the prompt to upgrade your QuickBooks subscription.

For more details on the upgrade process, you can click here. 

Once you've upgraded your subscription to Premier Contractor Edition, you can now add fields in your Vendor Profile to keep track of their insurance. Here's how:

1. Click the Vendors menu and then Vendor Center.
2. Look for the vendor's name and double-click on the vendor's name.
3. Click Additional Info. 
4. If the options are not yet added, you'll want to manually do so by clicking the Define FIelds option.
5. Enter a label of the field and select Use for: Vend.
6. Select OK and then OK.

After adding these fields, you set reminder alerts as my colleague AlcaeusF shared. You can follow the steps on how to set it up. 

For an overview of the transactions created for your vendors based on the fields you added, you can run and customize a vendor report. 

Keep me posted on how this works. I’m looking forward to hearing from you. Keep safe!