I had an item not fare well in the shipping process. I didn't stress about because I knew it had been insured by USPS. The buyer was relieved to get their purchase price returned and I didn't have to take a hit on the damaged goods.
A few things to remember when it's necessary to file a claim. 1. Whomever files the insurance claim is who the payment is sent to. 2.You'll need to mail a money order to the buyer. 3.USPS cashes their own checks with proper ID and sells money orders too. Then you mail the money order to the buyer. 4. Why does the seller usually file the claim--USPS requires proof of item value to be uploaded. A screenshot of your OfferUp listing is more than ample proof of value. 5. USPS is incredibly slow with this whole process now (used to be streamlined). It takes up to 5 days to actually receive the check in the mail from the date of when the claim is approved. 6. you have to constantly go online to USPS for any updates because they don't send email updates for some reason. 7. Keep constant communication with your buyer so they know what is going on 8. Everyone is happy!