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@Roosterrun
Interesting that vinyl is coming up as something that people have regretted selling. I did sell a fair few d&b 12's when I sold my decks a few years ago and haven't really thought about them since. I think I'm going to have a proper cull and perhaps just keep classics for now.
There really is so little about my possessions that actively motivate me or make my life more enjoyable (apart from my bike). I listen to most of my music and radio/podcasts from one source - my phone. My turntable gets used maybe once a week.
When I think about the things that actually bring me enjoyment it's the intangibles, the indefinables. It's the experience not the t-shirt.