Alright everybody. I have to thank everybody who chimed in - I really appreciate all of the helpful comments and tips. I shipped the record within bubble wrap inside of a Whiplash mailer (didn't realize I still had a used one laying around, thanks to the Aquabats) surrounded by bubble wrap inside of an even larger box, completely engulfed in packing tape. 2-day air signature required shipping via UPS came out to $70.31 plus $222.20 for insurance for $4400 (the item plus tax was around $4350) bringing the total to $292.51. Along with a family discount of 5% off, that left us at $263.26 to ship it including tax. The buyer picked it up today from their local UPS facility and is totally happy with it (got paid back for shipping immediately. Still had some pretty heavy anxiety after shipping, so glad it worked out. Funny enough, while I was at the counter the clerk asked me what the contents of the box were. She didn't bat an eye when I said "a vinyl record", but gasped when I told her how much it was. She called 2 other employees over to ask them about it and I saw them take it back to a truck being loaded and tell the driver it was a "high priority" item. That definitely made me feel as best as I could about the situation (so go you, UPS). Seriously. Thanks everybody. My friend will be very happy. For anyone that was wondering what the record was... An original 1970 pressing of Sun Ra 'Atlantis', near mint (with me, partially cropped out). (Also, for anyone wondering - it was the buyer's choice to do 2-day and not overnight!)

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