I have a long history of regretful buys, regretful sales, and re-buys. Some of those re-buys have been successful; others not so much. Maybe 50/50. Some items I've even re-bought for a 3rd try (even 4th in a couple cases) - those don't work out. I've learned to (try) and stop myself before a 3rd buy. It means there's something I strongly like about the component, but also something I very much dislike.
Big Tannoy DC speakers with pepperpot / alnico drivers are the cornerstone of my speaker setups. They have been for over 15 years, and are my "forever". Collected a few of them now, so can't tie it down to a specific one besides Canterbury / Kensington. Also love some of their cheaper "tulip" DC models, but for a main speaker I'll prefer the pepperpots.
Electrostatics are the cornerstone of my headphone setup (10+ years), but after a long time running Stax SR-009, I switch to ES Lab headphones. The longer I use e-stats, the more "wrong" other types sound. The real problem is amping them - it's hard to find an e-state amp that sounds really good, then hard again to keep it running. I've had more problems here than any other component type.
I love my SOTA turntables and really didn't need those expensive side-quests to other brands, though it was fun. Successful return-to's include Rogue Hera preamp and Hagerman Trumpet phono (the old wood tower). Their sound just jives with me, even as I've had / have MUCH more expensive components from other brands.

