I think you did the right thing by contacting the guy about the issue first, and then went above and beyond what most buyers would have done by sending a second thoughtful message. The "cost" to ship, and where that is accounted for in the selling price, is a debatable issue, but cramming $1500 of any product into a box such that portions of the contents are visible upon arrival without opening the box is inexcusable.
If it were me, I wouldn't have even brought up the cost of the shipping once it was reduced to $20. Whether you believe him or not, he does have a point about the insurance cost. The real issue to my mind is his packing, and it doesn't sound like he made any apologies for that.
It looks to me like you have 18 opportunities to explain to all of his buyers exactly what kind of care they can expect him to take in packing their purchases. That's one of the up sides of being abused on multiple purchases: you have more available characters to tell the whole story. I would never condone slamming a seller with multiple negatives without contacting them first, but if the guy's an unrepentent douche bag, he's got it coming. Just be honest and straightforward in your feedback comments and don't use abusive language, lest he should make a case to eBay for having your feedback removed.
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