Oh yeah. Bought and sold lots; some I re-bought later. Many components I regret selling; others I sold off and never really desired again (learning experiences). Then a few times I bought/sold the same damn component 3 times (or more) - that’s generally a good indication I like many things it does, but can’t live with it long term. The audiophile equivalent of a toxic relationship lol.
Many components only shine when used in conjunction with the right partners and right system. I’ve had huge swings in opinion on a piece due to this. So that’s my justification to keep a few (or several) of each component on hand at a given time lol. And also in being hesitant to let go, in general.
Some components get harder to find as time goes on - as interest wanes it becomes forgotten and drops out of general trade (they’ll probably hit circulation again when the last owner dies and it hits estate sales in the next 10 - 20 years). But generally, most lose value in the long run. The exception to this was some of the really esoteric headphones in the 2000s. I definitely regret selling many of these for "too low" prices back then. I mean like Sony MDR-R10, Sony Qualia 010, Audio Technica ATH-L3000, Grado HP-2...