When CPQ decides to just not work as expected, rerunning the install scripts from the Managed Package page should be a first stop.

The key indicators of when to run the rules is when

• CPQ throws an error with the phrase “Field Metadata” in it
• A price rule condition stops working or is not considered
• When you as an admin insert a bunch of fields or new picklist values
• CPQ just chooses to skip rules when they are active

Yes CPQ can sometimes act strange but there are some fixes out there.