In the early '70s, all my gear was stolen including a 68 Tele Thinline, ash body with a factory Bigsby. Got it back, but the guy had messed it up. There weren't luthiers on every corner back then, so I traded it off on a Gibson ES-150DCN. Horrible trade...the Gibson turned out to be an unruly white elephant. Regret selling the Tele. Don't regret selling the Gibson. Took a bath trading it for a 79 Music Man Sabre II, but that turned out to be a great guitar.
Also, around '73, I'd bought a virtually new long neck Gibson ES-330TD dirt cheap from a junkie. Great guitar! Traded it off for a Univox drum machine. Drum machine helped pay the rent for many years, but I really miss that 330. Never seen another quite like it.
I had to sell my 1960 Strat after my divorce in 1990. Miss it, of course, but the G&L Legacys I have now are better guitars. That Strat would be worth $20K+ now...ugh.
After my gear was stolen in '72, I bought a new sunburst Univox Les Paul copy. Beautiful little guitar with a bolt-on neck. Not the best quality, but it just had a beautiful clear tone. Loaned it to a young friend and it was stolen from his dorm room. (I HATE THIEVES!)
I miss the '72 Martin D-18 that I traded for a Taylor 710CE jack in 2002. Bought the Martin new. Hard to give up an old friend, but I needed a guitar with a pickup. Did well with the Taylor, but it will never be my favorite. I'm a Martin guy.
In another financial crisis, I had to sell my 1975 Gibson Les Paul '55 Special Reissue. I'd bought it used, mint, just a few months old. Traded a beat up but terrific sounding Acoustic Control 156 amp rig straight across for it...a steal for me. Had some problems with the neck, but that was the best P90 guitar I've ever played. Absolutely killer through my JCM 800.
And then there was a vintage 1965 Deluxe Reverb, and a blonde, BF, 1964 Tremolux rig. Oh well. I love my Mesas.
Bill