In my imagination you chose the guitars you bought because of how they played and sound, but I'm not so sure about that now...
Not entirely, no...
In many cases, yes. In some cases, yes and no - I also paid attention to the value. Many of the guitars were used, from other musicians. So, playability was important. At the same time, value was also important - but that value was very different than today.
I had no fucking clue that a Wylde guitar would be worth 80k. I just knew that it was in good shape and had features I liked. i also knew it was a good investment - but not that good.
$500 bucks to $80 grand is a hell of a good investment. That's almost the return congressmen get!
It's pure luck, in a way. I took what was made available to me - in the era that these guitars existed. So, some of 'em are quite special.
I have some Martin examples that might only break even on the open market, but I regret nothing. All told, the examples I do have counter those that didn't keep their value.
At the same time, it has LONG been known that a Gibson Les Paul is an EXCELLENT store of value. If you buy a $2500 Les Paul, it's worth at least that much. If you change your mind and sell it six months later, it's worth at least that much. That's the Les Paul world.
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