1959 Volvo PV-444.
The Mickey Mantle and Willie Mays rookie cards that I put in my bike spokes.
I managed to keep most of my childhood possession intact, but there is one thing I miss.
I had a paperback novel, Sinbad & Me, about a teenage boy and his bulldog who solve a mystery. I loved it as a kid, but it got sold. I’d like to reread it, see if it still is good from an adult perspective.
Would you believe, that is one expensive book! I’ve never seen a copy available for under $200! I wish I still had it just to read it, not to sell it for money.
Maybe in our glorious coming future, it will again become available. Maybe digitally. I eagerly await that day.
My parents were antique dealers, collectors and hagglers. Well, my dad was the haggler, for sure. Unfortunately, he sometimes went one trade too far - flipping something he shouldn’t have.
I can recall two: a sperm whale’s tooth that had been scrimshawed - one side was a picture of a boat, and the other was a whale and a longboat, struggling in a rush of water. I think it was from the early 1800’s - I had found it at a big collector’s fair for nothing (I want to say $35?), and dad agreed that it was worth more and cool, and got it. Primitive, but as a little kid, I loved that tooth. Dad flipped in a deal for a pocket watch - also cool, but man, that tooth.
The other was a signed Book Club Edition of Steinbeck’s Tortilla Flat. The true first was going for thousands at the time, unsigned. Dad got this one for maybe $100 - a good deal. He and I each collected books, but had little overlap in our interests. This was a cool overlap - TF is probably my favorite Steinbeck alongside Cannery Row. I said I would like right of first refusal if he ever was going to flip it (I knew my dad) - but he got a great deal selling 10 signed Steinbecks as a package and needed the money to redo their bathroom. But man, I would’ve loved that connection to my dad and book collecting.
So yeah, they had value, but it was what they meant.
I gave my entire stamp collection to my nephew when I went into the military at 20. I had worked on that thing for at least ten years, and a lot of the stamps were mint. He sold it to a friend of his, the knucklehead.
I kinda wish I hadn’t gotten rid of my metal detector, but it collected dust for ten years.
I don’t really regret getting rid of anything. It’s all just stuff and it starts to own you after awhile. While I wish I still had my Lionel train set, the Fort Apache set, and other childhood toys that are now worth a bit of money, it’s only for the monetary value, and I don’t regret that they’re gone. I wish I could get rid of more, rather than still have what I don’t need.
My Hardy Boy Book collection. I had 1 through 50. Took me years of my allowance to get them all. These were the hardbacks. Not the paperback crap they sell today.
Donated the collection to the library when I was 19. They still aren’t really valuable. Its just sentimentality for a piece of my childhood.
That really is true; it’s all just stuff. (I just remembered George Carlin’s brilliant “Stuff” routine.) In 1985 when I was 27, I lost everything I owned in a fire, including a dog and a pick-up truck, except for a pair of cowboy boots that were in the shop getting re-heeled. Sounds like a country song, but was traumatic at the time.
Really though, I eventually realised it was all just stuff, except for the dog. 
The only thing I even remembered owning and missing a couple of years later was an album of old family photos, including photos of my dad when he was two years old.
16th Century, signed, wakizashi.
Porsche 911SC.
1942 ‘byf’ P.08 Luger pistol.
Years and years ago, I sold an Ancestral Recall for $95.
I’ve mentioned this before:
My father had a box on his dresser containing some uncirculated 19th century silver dollars. He had warned me not to handle them because it would decries their value. Well he didn’t warn me about emptying the box and spending the coins . . . AT FACE VALUE. I wasn’t smart enough to sell them, I just spent them.
Yes, I couldn’t sit down for a week.
When my ex moved out, I gave him my bicycle. I was moving to Manhattan, and didn’t anticipate driving it in city traffic. After he moved, he took it to a bike shop for a few repairs. The salesperson talked him into thinking it was the wrong size, so he took it off my ex’s hands for $20. I had paid over $400 for it.
Same for me I have about 35 or 40 of the 58 in the series. All hardback and some of the very early ones too (for example I had two versions of The Twisted Claw - sometime in the 60s they re-wrote many of them to make them less racist and more socially modern).
Well, you could have offered him the same deal. If you’d thought about it in time.
In the late 70’s, at about age 13, at my grandmother’s house, my (one year younger) aunt and I found some old 45’s. One of them was Tony Sheridan with The Beatles performing “My Bonnie Lies Over The Ocean.” We thought it was hilarious!
By the time I realized, a few years later (I became a major Beatles fan around the age of 16), what I had held in my hands, grandmother had moved into a trailer, then passed away, and it was long gone.
I wish I hadn’t sold my coin collection in early 1979, just before the Hunt Brothers tried to corner the silver market and drove the price from $6/oz to $48.70.
I sold a bootleg double CD of Beatles White Album outtakes on Ebay auction over a decade ago when I was a new seller. It went for about $15, and I haven’t seen a copy of it online since. I’ve seen some other bootlegs but they don’t have the same tracks.
That’s it. Thread’s done.
The bicycle I had when I was a kid in the 70’s. I cant believe what those go for now and I think we sold it for about $20.
My Honda 90 cc trailbike. I should have known something when we sold it 5 years later for more than I’d paid for it. It’s a collectors item now.
My Evil Kneivel motorcycle collection which know goes for a high price.
My Hardy Boys collection which I sold for $1 a book.
When I was in high school, I bought an album (on vinyl - this was the late 60s/early 70s) that Davy Jones recorded before he was in The Monkees. But when I joined the Navy and left home, I gave it to my aunt - she was mentally handicapped, but she loved the Monkees. Unfortunately, I’d forgotten that when she decided she didn’t like a group any longer, she would destroy anything she had related to that group - she did that with her Beatles collection and, alas, she also broke and tossed the Davy Jones album.
I really wish I hadn’t given it to her. Not that I’ve pulled any of my vinyl out of the boxes they’ve lived in for better than 10 years, but still. However, this thread got me looking and I found it on EBay for not too much, so I’ve ordered it. Wonder if it’ll come up in a future thread about things you wished you’d never bought… 
I had one of thesein my big box of lego - I have no idea what happened to my childhood lego collection - I have rebuilt much of it recently, but not this item.
I played the collectable card game Magic: the Gathering in the mid 90’s when it was relatively new and sold all my cards a couple years later. At the time, a lot of people assumed the game was on its last legs. Still going today and, where I sold all my cards for maybe $300, that collection included at least 25 cards that today sell for $100-$400 each.
I wish I still had my '67 Caprice. It was a four door hardtop (no center posts) with A/C and a 327 with double-hump heads. Sold it for $650. The other car I wish I still owned was a '63 Lark Cruiser V-8.
Somehow in moving, I lost a 1920’s Underwood typewriter with chemistry characters. The top row keys, except for the 1, had only a single numeral on them. The one also had a yields arrow sign. Use the shift key and the numbers became subscripts, except the first key. It was either a subscript 1 or a yields sign. I still wonder if whoever ended up with that thing realized what they had.