Don't beat yourself up.
A lot of people think that their cartridges are unusable once linked to the Gypsy. That is a common misconception and an understandable one.
You can transfer your CCR (laptop save files) to the Gypsy. You do have to use Cricut Sync. It's really easy. I don't know if you have to update the Gypsy though. My Gypsy is updated. I just updated it when I took the Imagine app off. You could try saving through Cricut Sync to the Gypsy and if it says to update just cancel out and unplug the Gypsy.