The item of hifi I regret most selling is my CDS3…
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My Akai GX95 tape, Nait 2 CB, Nat 02…ah, my Philips CD 104.
Like Richard, a CDS3
Sublime sounding thing. Took me years (and a lot of money) to get back to that level, and even if I love the convenience of my NDS and NAS I have no doubt the CDS 3 would still sound amazing in my system. Or any system.
Bruce
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It’s quite a list: LP12, Nait, Kans, SBLs and CDS.
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Wow — that’s an extreme response. How big is your loft? 
Linn Kan I
Naim XS2 — such a lovely amp, and my first piece of Naim. My sense is that the XS2 is somewhat underrated here. Should have kept it for a second system, but didn’t anticipate the urge to have Naim in the family room. Instead I might get something cute and olive for the family room when the right opportunity pops up in the fishy place…
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CDS2 CD Player
If it was yours that went to HH I have them! Bought them from him in 2007
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Exposure X
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Probably my kidney 
But seriously
Naim and the LP12 have a pretty clear ladder / upgrade path for us all to climb, maybe there’s a couple of sideways moves 52-252 & 135’s-300 I wasn’t ever tempted by those
I had a brief regret selling the Superline/ Supercap DR
I couldn’t justify having a £21k pre without a similarly matched Phonostage
I bought a Tom Evans Mastergroove, I had made certain I could take it to SR spec prior to the purchase
It took 5 months to do, then I sent it straight back,when I eventually got it back again I still wasn’t overwhelmed
Some things were much better but low end clout was certainly missing
At this point I didn’t know it would take 6 months to burn in properly
So I bought another Superline/ Supercap DR
Although by the time they arrived and as the days progressed it became clear the SR was way ahead in most aspects and its short falls we’re getting less and less
And soon the Superline and Supercap went
So not really a regret just a partial
Lyndon
DAC V1, my first Naim
A 1988 vintage Nait 2. It’s not that I regret selling it, I regret selling it in 2001. And I regret selling it to an acquaintance for £100. If only I’d hung on I coulda got an awful lot more for it…
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My entire first paid for by me system. Many happy memories. Linn Basik v1 with Akito arm and Goldring 1040, Cambridge P40 before Richer bought them and B&W 603 first edition. Had to get rid of it when I moved into a tiny place. 
My last tin of gramaphone needles, oh, and my Pioneer PD91 CD player with outboard power supply (loose coupled at the rear as you can just see).
The reason for regret ? Both would now be worth many times what I paid for them. 
Michaelson & Austin TVA1 50W valve power amp.
Sounded pretty good but needed a new valve set and a spanky new NAP110 was better in every way. However, in all its black and chrome glory it was the absolute perfect match for Gale 401s
Pioneer A400.
@TimOopNorth Could be them. I bought the Totems in August 2006. I will have dithered for a bit but I know the person who bought them didn’t keep them long. I thought I still have the serial numbers but a quick search hasn’t unearthed them.
Whether mine or not, I hope you’re getting the same pleasure from them I did. The Totems are better in many ways but still but…I do miss them.
Guru juniors
Complete old school quad setup. Quad II amps with the GEC KT66 Valves, 22 preamp (with Mullards) and tuner.
A customer wanted to trade it in when I worked in hi fi 20 years ago. It sounded hellish through a variety of speakers until we stuck it through some Mission 774s and it was quite decent. I bought the lot personally with manuals and catalogue off the chap who was quite happy to go for a Linn Classik I think?
It lived as an ornament for a few years occasionally running AE1mkIIs in an audiolab setup, although I was always concerned about them burning the house down if I fell asleep listening to soothing music. They sounded good at normal listening levels, really well engineered considering their age. A couple of slight hisses could be heard on the odd occasion but they worked perfectly.
I ended up selling the lot (with tuner untested) on eBay at a slight profit in hard times. I’d get around the same for the valves now.