Mine involves an XT System I bought off E-bay and later sold before moving to Washington.......
For about $35, I bought a hacked-together, abused XT clone in a flip-top XT style case in 2004. How that thing survived the trip to Opelika unscathed was a mystery to me as when the UPS man brought it up the drive, it was in a beat-to-hell box, leaking foam packing peanuts everywhere down the driveway, and zip-tied. I swear, I could have done a better packing job if I were blind and had one arm!
So I owned this machine for 2-3 years and it cleaned up quite nice. I found a 5153 CGA monitor for it for free at a garage sale, and pieced in other parts sourced from a little hole in the wall shop downtown full of surplus PC hardware. Then the fateful day came that I needed to move to find more lucritive work prospects, so I sold it on e-bay, and Packed it 1000% better than the nightmare above.
Well, both arrived at it's new home, the back corner was bent, at the hinge for the case, the 5153 was destroyed in transit as well, neck of the tube broke off and everything), the only thing that survived was the least packed item of all - the 83 key XT Keyboard! I wound up giving the poor guy a full refund and losing one of my most prized machines in the process. I still wish I had that thing now after that happened to it!
Damn you UPS!!!!!
Speaking of UPS horror, I've had multiple reports from my Fiancee of them dropping off presents at our door, some of high dollar value, without even bothering to knock! Or bringing them to the office without even trying delivery. It's one reason I don't buy/sell on e-bay or anywhere else anymore, I don't even trust a courier company as far as I can throw them.
Hmmm..now I'm thinking of more vintage computer related horror with shipping.....
Then there was the time I bought the case my current XT is in, it was shipped from Monterey California in late August 2005. It was a new-old stock SongCheer XT Chassis. That same month, the sweet old lady Drexel up the street died. So I am walking around the block and see a box on her porch suspiciously the size of my computer case, and with chinese lettering on it! I pick it up, sure enough, addressed to me, address is correct, and it had been sitting on her porch how long now? Yet another reason I don't trust courier companies.
I've had some good onves involving guitars too.....
Bought a CAsio DG-1 Digital Guitar (pretty darned rare) off E-bay 2 years ago. The UPS Guy knocks at 8am on a Sunday, and THROWS The guitar at my sleepy ass when I open the door! (shaking fists)....
Then there was the Bridge for a 1971 Fender Musicmaster I'm rebuilding. They (fedex) could have just dropped it off in the apartment office like they usually do....NOPE! I had to drive a hour in rush-hour traffc to Bothell almost 10 times to pick up the damned bridge! For s stinkin' Guitar Bridge! Heck, they could have put it in my mailbox, or shipped it via USPS so that would happen.....nope.
And lastly was the Hondo Paul Dean II....an apartment OFFICE fail, and a very rare guitar designed by the Guitarist from Loverboy in the early 1980's, that I bought 2 falls ago. The tracking said FedEx delivered it.......nope, no sign of the guitar in the office. I had to wait two days to pick up my "delivered" guitar because of one of two things.....either the Apartment Office was lying (and too dumb to know what size a GUITAR box was), or FedEx was closing their Queue before actually delivering it. Either way, this is the reason for my profound hatred of couriers.
Now, anytime I order or send something, it's paranoia till it arrives at it's destination.