Has anyone had a problem where an expired credit card fails, but in your settings you cannot delete the old and add a new?

You cannot use your Chromebook, you can't install iTunes on a Chromebook, you need a Windows OS or macOS computer.

Try to do from your iPhone.

See -> Related Article: If you need to change or update your Apple ID payment method

• If you want to change your card, add first the new card, then remove the old one.

See also the following Apple articles:

Remove a payment method from your Apple ID

Remove a payment method from your Apple ID - Apple Support

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If you can't remove a payment method

If you have subscriptions like iCloud+, have an unpaid balance, or you use purchase sharing, you must keep at least one payment method on file.

• Do you have a subscription? You can cancel iCloud+ and cancel other subscriptions from Apple. When your subscription period is over, remove your payment method.
• If you're in a Family Sharing group and you use purchase sharing, the family organizer must have a payment method on file. If you're the family organizer, turn off purchase sharing, then remove the payment method.
• If you have an unpaid balance, you might not be able to remove a payment method. Instead, change your payment method.
• 👉 If you still can't remove a payment method, contact Apple Support.

Payment methods you can use with your Apple ID

Payment methods you can use with your Apple ID – Apple Support (UK)

fyi: Not all credit & debit cards seem to work with App Store / iTunes Store, try a different one, or preferably a credit card. If your card is not accepted as a paymenf method, you need to contact your bank.