Here's my list:
1965 Gretsch Country Gentleman mint condition: $150 purchased in 1985. Sold in 1998 to help pay for a semester in graduate school. (I didn't like that guitar much).
1966 Gibson ES 120T also mint condition. $100 paid in 1983. A thinline beginner jazz guitar with a single Melody Maker P90 pickup in it. Had this large black polycarbonate (I think) pickguard where the single tone and single volume control were mounted along with a 1/4 input. Sold in 1985 to a gentleman who lived in a trailer park who responded to my ad because he had one when he was younger in the 60's. I used the $150 I got from it so I could fund a Martin D 28. (In the mid-1980's these ES 120T's were very cheap, no one really wanted them. I am surprised that they sell for around $1000 + - now).
Mid 1980's Hascal Haile Classical: $275 paid in 1986.Hascal Haile was known for building guitars for Chet Atkins. I remember back then, I took the guitar to R Brune to evaluate it and he said something like "looks like something built by a furniture builder, we have no market for this type of guitar here, maybe people who read "Frets Magazine
would be interested in this". Sold it in 1988 to help fund a down payment for my first new car, a 1988 Toyota Tercel. (Wow!)
1965 Fender Jazzmaster. Not great condition: Purchased for $100 in 1979 when I was in the 11th grade in high school, from a small neighborhood music store in Chicago (remember those?). I had just seen Elvis Costello and the Attractions at the Aragon Ballroom in Chicago a month earlier so I figured it must have been cool guitar, just like his. Back then the guys in the neighborhood all wanted Les Paul's. The neck needed work and the original knobs were changed to silver Gretsch Knobs, but I didn't know that these were non-original at the time. The hex screws on the bridge were a bit corroded and would pop out when I would play it. Back then, I didn't know anything about where to have a guitar set up, and actually, I don't think there were many luthiers in Chicago like there are currently for electric guitars. It sounded great though a 6L6 amplifier, but the action was wonky. I sold it to a guy for $125 in 1981 though a print ad in the Chicago Reader (the free weekly distributed in Chicago at the time).
In the early to mid-1980's I was familiar with a lot of musicians playing pop and rock in the Chicago area as I had a good friend in the sound business at the time. At times I would help him out on shows for a few dollars. Many times he would indicate to me that a musician was needing to sell an instrument for various reasons and that was how I came across these instruments. Except for the Jazzmaster, all the other instruments were from local semi-professional rockers, including the Hascal Haile.
To be honest, I don't miss any of those guitars. . . .