Mint Nait1, 2x Nait2, 1969 Speedmaster sold way too cheap in 2015.
Many years ago, I had a Bang and Olufsen Beogram 4000 turntable (the parallel tracking one.)
I foolishly sold it due to being restricted to B&O cartridges. I now wish I had kept the deck and bought something like a Rega Planar 3 to feed my Upgraditis !
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BMW M6 Coupe 
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Mosaic box set count basie. Now i have naim the jazz sound wonderful.
At the time i had a very cheap portable cd player. So the sound was not very good.
My good albums i put in auction. They fetched very good prices.
Some collectors sell their collection. Because the partner wants to travel. Camel riding.
Mountain climbing. Etc.
I get chided for not flogging (or just binning) about 50-70 truly dire awful albums. Things I bought between the ages of 12 and 18 several decades ago.
But your music collection is like a log of your own past. The good, bad, and the ugly. The one thing I can’t sell is my past. Embarrassing musical phases and all. The further back your collection goes the more content you might not want seen by guests. But own it (literally and emotionally) I say.
Plus, you encounter this odd phenomenon where utter trash (at the time) that was your guilty pleasure gets re-evaluated and suddenly gets widespread musical approval. Takes 30 years usually though.
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I keep my early Records because it reminds me
Of my school days. In the 50s.
Sometimes i do not like to look back.
The school dinners. Fish pie and camp coffee.
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The attachment is to my H fi. In the spare room.
Not in the loft. The car has gone to my wife.
I do not regret selling my country music CDS.
The Systemdeck IIX + Helius Scorpio II, this is something I really regret. Sold in 1992 to finance an ex-demo Linn Sondek/Ittok/Trampolin/Lingo/Asaka that proved to be superior, no doubts, however I should have kept the Systemdeck, a lovely turntable.
That combo with the help of a Grado X+ granted me great listening sessions.
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