There are lots of shipping Insurance options out there now that don't reflect on the label that can factor into the shipping cost. It can cost $15+ bucks to Insure $1500. ShipInsure through Stamps.com or Ebay can sometimes cost more then the Post Office rate.
Sounds like he did a crappy job packing the box up though, and there's really no excuse for that. He should have paid the few extra bucks it might have cost to pack the cards more securely. If he was worried about the cost he could have sent you an invoice for $25 bucks to cover the extra cost, instead 20 bucks.
I have no idea how he could fit 18 graded cards into a small flat rate box. That's crazy. You're not supposed to break the seams on flat rate boxes and envelopes without getting bumped up to straight package Priority rates.
I'm also surprised he didn't use Signature Confirmation. That's asking for trouble with Paypal on a transaction of that amount, unless his private insurance doesn't require it for some reason.
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