for me, i used to sell as soon as i could tell resale value was on its way down.
I'd sell the item, get the money out, and buy it back in a few years when the value decreased, so i didn't have to eat the depreciation.
for example, buying a boogie mark V the first year it came out. I had it for a few months, sold it for what i paid, then 2 years later, bought it again for 600 less than the first time.
same with the kemper. bought it when it first came out, played with it for a few months, got it the hell out of here, and then bought it again when the hype leveled out a year and a half later, and the price came down a few hundred.
or the opposite. if i know i got TOO good of a deal on something, and i can make a boat load of cash reselling it, its gone no matter what it is.
examples: stock 65 fender dexlue reverb i found for 500, and knew i could get 2k for, so see ya! I would have loved to keep, but thats $1500 i can play with now!
idk...i'm weird. I don't get too attached to anything, cause its all just material.
I only have 1 guitar, 1 amp, and a delay pedal now. When i started focusing on my culinary career (chef now), and then had 2 kids, time and money for gear went out the window. Selling stuff off for bills, mortgage payments, car repairs, home improvments, other grown up bullshit that is no fun.