Whatever you do, ALWAYS insure your precious investment-grade art under your homeowner's policy. Currently, I own $108K worth of recovered artwork personally. Never would I consider going to USPS or FedEx to recover such worth. All insured through my Allstate homeowner's plan for FULL RETAIL VALUE. Then, if the painting is lost in transit you pay the deductible and collect the total net sum. Folks can literally hit the jackpot by "losing" items in the mail...done all the time, every day of the week. You'd be surprised how many owners WANT their paintings to be lost forever.
Trying to obtain your lost art is, well, a "lost cause". You won't get hardly a chance after UPS turns in the paperwork. I tell people it's like when your car is totaled. You don't get to keep the check and the car, do you? No. Then the insurance company sells the car to a guy specializing in totaled out wrecks. Yes, you do lose the painting, there's no getting around that, but at least through homeowner's you get a fat check to wipe away the tears.
You asked about specifics, wow, I get some the greatest deals you've ever heard of in your life, Zoe. I have in my possession a $20,000 painting that was to premier at a New York top tier gallery show just after 911 hit the city. I told the artist I wouldn't mention her name in any correspondence so I won't...let's just say she's quite well-known in the Palm Springs, Florida area. Well, the husband had rolled the canvas and placed it into a pvc plastic tube for transport via UPS. After 911, every piece of suspicious-looking mail piece was searched...and this certainly fit the description! Painting didn't make the show, it was printed in the catalog, the artist and her husband were at the show...no painting. Years later the painting shows up and presented to me for acquisition...for $1000.00! She was given $300 by UPS at settlement.
Earlier in 2007 I acquired an original Andy Warhol trial proof for $6500.00, had some surface damage that needed attention, but the country's top preservationist in San Francisco personally told me it could be done for about $3500. Sold it to a West Hollywood dealer "as is" a month later for $11,000.00. He'll have her firm fix it, he'll put it in the hands of a collector for about $22K. We all make some off it. Bada-Bing! The art I have seen. If I kept everything, my home would have to be opened 6 days a week and charge admission!
Insurance through your shipper will not cover anything. It's hard to recover, it's minimal at best, they don't care at all what is in the box. And that's straight from my best FedEx guy. FedEx, by the way, is the best. I only use them to ship paintings that I must have delivered on time and safe. Try to stay away from UPS if I can help it, although my owner there is rock solid with merchandise other than fragile. Never USPS, you talk about not caring. Postal service is run and operated by union hacks who don't care one little bit about care. DHL, never used 'em. Yellow Freight on the big stuff is ok in handling but you'll never get a dime out of their recovery division. I've dealt with almost everyone in the business on luxury merchandise so that's my best qualified opinion of the biggies.
I'll be writing a book when I retire from this specific business...no time soon the way UPS is losing parcels! When I get a call, 6 out of 10 times I buy the art. At those prices I really can't lose, although a few bite you from time to time. Just as in any re-sale type environment, you're going to lose on a "sure thing" in rare instances. Recently I bailed out of a 1855 oil on canvas that I just could not get verification of artist, but was quite wonderful. I shipped the piece to London, had their top people all over this canvas and the best they could give me was an "in the manner of" or weak "attributed to". I broke even and unloaded it for cost. That doesn't happen often, though. Bought that one for $900 and sold for $1200, not enough profit for me to get out of bed.
I've got some great insight to how the insured luxury art business works from both the shipper's point of view, the artist or owner's, and ultimately into my hands. Most previous owners are cordial with me, but some are downright hostile and ready to hire an attorney on me. Had a world-famous Bulgarian artist cuss me out royally because he had to accept three $300 checks from UPS over three lost oils. Two at $2350 per and one at $1150. I bought them all for $700...still own two after selling one for $1500 to cover. What a life, huh? I go from home mortgages to recovered artwork to government landscape contracts...keeps me busy, Zoe!