Without proof of value, you may never collect any insurance

Don't decide at the Post Office whether to add insurance "just in case".  It's too late.  Find your receipts first.

You need to prove value for collecting both UPS (brown trucks) and  USPS (post office) insurance, but UPS might be harder: 

UPS INSURANCE

UPS insurance is free up to $100.  You can buy more (over $1 per hundred coverage), but you may never collect. 
You are warned to have an original receipt for the item, a signed receipt from the guy across the counter when you dropped off the package, perhaps the original complete packaging saved exactly as it looked at the other end, perhaps a police report . . .   

POST OFFICE INSURANCE 

Thank you, TK, for sending in this:

In order to make a claim when USPS loses your package, or destroys box and contents, you must have a receipt showing the value of the item.  Regardless of how much value you claimed, and thus how much you paid for the insurance, the USPS will only reimburse you for the value shown on a receipt.   "Would you like to add insurance to that?" means, "Do you have a written receipt for that, or may I swindle you?" 

Collector's items only have value between you and the collector. 
You won't be reimbursed a penny, unless you get a third party expert to swear this is how much the item is worth. Since it's in a zillion pieces and is worth zero, you are now late to the game of finding such an expert.

Getting items privately appraised in writing for every sale is impossible for most of us.  So
sell collectibles online and print the listing page.  But sometimes the final sale price is not shown, so get your PayPal page for that transaction.  If you waited too long and the transaction page is gone, print your  account page and add whatever  eBay/Bonanza.com/etsy listing pages you need to link that line item on your PayPal account page to the item. 

ADDRESSES  INSIDE TOO
Customers should ALWAYS put their name and address inside every package they send (preferably tape them to the items inside). That way if/when the packaging is destroyed by machines at USPS, and the contents get separated from the packaging and end up heading towards the Lost in the Mail Division, USPS will have a way to get them back to you.  (That's reader TK's advice to us all, and she's not making it up.)

SORRY TO NAG, BUT
Don't put the thing into the carton and then finish packing it.
First put packing into the bottom,
then cram The Thing and even more packing into the carton.

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JIN, rev 10Apr2017,  Feb2018.