I regret selling my '67 Plexi in 2006 for £1600, it was SO nice - was perfect at any volume, just the sweetest tone ever. I could cry thinking about that amp, but I was skint - really skint :(
Sold my Epi Japan LP junior a couple of years back for a little more than I paid for it, but it was a gorgeous guitar - should have sold my Tele instead, but I stupidly thought that I should keep the Tele as it offered more tonal options across the range of guitars I owned. I still have the Tele, its a great guitar, but my heart is with Gibson-type guitars.
Lastly, the 50w Silver Jubilee head I had back in the early 90s - it was my first valve amp and sounded amazing. The other Silver Jubilee amps I've had since never had the sweetness of the first one. I was into bl00ze at the time and sold it for a '63 Twin - also a great amp, but I'm not arsed about having the Twin back, whereas I'd crew off my left bollock to have the Jube back :lol: