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Shipping Issue.. Venting, but would love some feedback as well.

The neck joint is breaking loose. The finish crack runs at a different angle making me think they are only remotely related. Perhaps the joint was getting loose and that caused the crack but then I'd expect the crack to be along the joint, not perpendicular to it.

Neck was banged somewhere along the line. And it has been 2 months? You owe the seller nothing. You can go above and beyond by giving him $200 (or less) toward the repair.
 
Can you post photos of your packing job? What measures did you take when packing the instrument inside the case? I assume you packed the bass in a hardshell case, not a gig bag, right?

BYW, my stance on this is that the buyer should have inspected the bass as soon as he got it. Since there was a subsequent shipment of the bass (overseas, too!) you are totally relieved of any responsibility. Don't get sucked into any guilt regarding the crack to the headstock.
 
You were responsible for getting the bass to him in the condition you and he both agreed was acceptable (picture 1). If he opened it within a few days after that first shipment, and found it didn't get there OK, then you should make good - up to what you charged him. If he shipped it again, and is trying to put you on the hook for damage 2 months later, I'd politely disagree - it doesn't seem he's held up his end of the bargain.
 
OP, you sound like a stand up guy but you insured the bass for a reason, and it was on the buyer to check it at that time. Even then, the proper to do would have been to file an insurance claim. The buyer needs to understand that you were an individual selling a bass, not Guitar Center with a 30 day return policy.
Especially when it's been over 45 days!

YOU OWE HIM NOTHING. He was to inspect the bass when it was received so that insurance could be used to repair any damage. YOU DID NOTHING WRONG.
 
The word "if" rings loudly here...
You were responsible for getting the bass to him in the condition you and he both agreed was acceptable (picture 1). If he opened it within a few days after that first shipment, and found it didn't get there OK, then you should make good - up to what you charged him. If he shipped it again, and is trying to put you on the hook for damage 2 months later, I'd politely disagree - it doesn't seem he's held up his end of the bargain.
 
The issue, which we'll never know is if the damage occurred when you shipped the bass to the buyer, or when the buyer shipped the bass to himself overseas. If the buyer would have inspected the bass when he first received it and it had the damage, then we'd know it occurred when you shipped it to him and that would warrant an insurance claim and some recourse on his part. If the buyer just re-shipped the bass in the original packaging to his place overseas, never opening it or inspecting it, THEN finally opened up at it's final destination, I hate to say it, but that's on him.

All he had to do was open the box when it got to it's first destination and do an inspection. If he did that and saw the damage, I bet he'd have been in contact with you immediately.