Good post. I also get tired answering these questions all the time, so I recently saved my comments. Here, through the miracle of copy-paste, are some of my thoughts on the matter (I edited it some based on your post);

My take on insurance:

¶ the following points don’t apply if you have oodles of the inexpensive chip in question, so many that you will never deplete your supply over your lifetime. Then you can simply send them out uninsured and replace lost ones handily with no fuss.

¶ be smart and don’t buy or trade expensive chips based on lofty principals of commerce. Regardless of the law or prevailing ethics, take the time to make sure that chips will be sent insured -- get it in writing or by e-mail. (Of course, if you are the buyer, you don’t have to get it in writing if it says you get insurance in the auction description.)

¶ if nothing is said or asked, it is each person’s responsibility to have the chips he sends delivered.

¶ it is foolish to forego a good deal because you don’t like the shipping/insurance rules. Why cut off your nose to spite your face and let a $100 chip get away because the seller, who is asking $50 for it, wants you to pay $5 for postage-insurance? Just look upon the total cost ($55 here) as the cost of the chip.

¶ For really big transactions, I get firm assurances that the stuff will be sent insured. (Pride go before the fall, as they say.) I just won a $200 old gambling book on eBay. The auction description said “Good Condition. S&H $2.00.” The seller billed me $202.00, which he said included S&H. I emailed him whether that included insurance, which I wanted. He emailed me back “yes, it did.” It was smart to ask outright and not rely on armchair chip lawyers that “of course he has to insure delivery.” If I didn’t get the book, I could be legally right, and I still wouldn’t go through the effort of suing him.

¶ another thing is that too many buyers are just too cute (and lazy too) about not asking about insurance. They want to have their cake and eat it. They are afraid to ask the seller (who already planned to sent it insured at no extra cost) to insure it because they are afraid their question will put it into the seller’s head to ask for extra money. So by not asking, they hope to save some money, and then hope that the seller will make everything good if the parcel is lost or damaged in the mail. The better approach is to iron out all problems in advance.

¶ I think the seller should insist that all valuable items be sent insured, and he should either bill the buyer or (if he is happy with the high price) to be a gent and pay the shipping-insurance costs himself -- it is his choice. It is easiest for the seller just to ask for, for example, “$2.00 postage-insurance.” Don’t complicate things with offering options such as waiving insurance, adding or deducting $1.30 to the price, etc.

¶ Insurance (for stuff over $10 - $15 - $25, anyway) does give peace of mind and protects against the glum feeling that someone lied to you about not receiving a parcel. The insurance might not pay off in the long run in a dollars and cents way, but pays off in an intangible way, particularly if you are the nervous type.

¶ It is a chore to go to the post office to insure things, so just let your outgoing parcels pile up, and go to the post office once a week or so.

¶ another advantage of insurance is that the green and white insurance receipt slips make a nice shipping record of stuff you sent out. Even if I don’t avail myself of the insurance, I write a big “UI” (for uninsured) on the green insurance slip. When I get home I file all the slips (the insured slips and the “UI” slips) in one folder. On the slips I have notations as to what I shipped, the address mailed to, the fact that I left feedback and/or emailed the recipient a “heads-up” that it was sent, that I was paid by check or PayPal, etc. Very handy, those little slips. Good control.

Robert