RE: ..
I am not sure I agree with the responses you have gotten.
I think the issue is whether the merchandise is normally insured or not and whether you knew it. If he told you he was not going to pay for insurance based on your friendly deal, then the loss is yours based on your willingness to except that risk in exchange for the lower price. But if he, as a normal business practice, does not insure his shipments and you as a buyer (with or without a discount) has a reasonable belief that shipping loss is the delivery company or seller's responsibility, (friendship aside) he is running the business and is deciding what risks he is willing to assume regardless of whether he is giving a discount, selling a discontinued item at a discount, getting returned merchandise, warranty claim, etc. Another words, if this was not a "friendship" discount but a discount based on a discontinued item or Black Friday sales price, would you be any less entitled to think that any shipping loss was going to be "split" between the two of you?
Whether or not I am getting a friendship deal, dealer discount, close-out bargin, etc., I believe any shipping loss is between the seller (friend or not) and the shipper he uses UNLESS I am told that any possible shipping loss is mine. Regardless of the discount, you didn't get the merchandise you paid for. Unless you, the buyer, knew and accepted that risk, that's the seller's cost of being in business if he elects not to insure his shipments and he doesn't inform the buyer it is buyer's responsibility.
I know where your friend is coming from...he probably doesn't insure his shipments and at the discount he sold it to you for, having to replace the merchandise would cause him a loss unless you shared in that loss. But you didn't get what you did pay for and if he didn't tell you shipping loss was your responsibility....bummer.
I ALWAYS verify who is responsible for any loss when I return merchandise but I assume the original shipment is the seller's responsibility.
However...ultimately you have to decide what the "friendship" is worth as well.