It's a tricky subject, and something that i'm dealing with at the moment as well. I have a friend who is passing on some instruments that may or may not need it done. And I might want to purchase those instruments...so what's the risk? Having purchased a guitar last year that had the neck reset (gone wrong) already, i'm still finding little issues with it. Besides the disclosed issues when I bought it (cosmetic damage that was skillfully repaired), the frets were leveled above the neck joint, but never recrowned. Things like that on this specific guitar don't bug me because 1) I'm not playing above the 12th fret on an acoustic guitar...like literally ever and 2) This guitar is STILL fantastic. I'm still smitten with it and 100% satisfied with my purchase, price, etc. I'm lucky that all of the "issues" i've found are either cosmetic or don't matter at all to my playing style.
But there's the rub. Neck resets are incredibly common with older guitars. But that doesn't make the process any less destructive. You are literally breaking the guitar - parts that were never meant to separate. Anything can happen during that process. So if we are comparing a guitar that needs a neck reset vs one that's already had one, it's a tossup. I'd posit that, assuming it was done right and CAME OUT right in the end, the guitar with the neck already reset is more valuable than even the cost of the unreset guitar plus the cost of the reset. When you shell out cash for a reset, it's a gamble. The more skilled AND EXPERIENCED the luthier, the better your odds.
I'd say, unless you have an extremely competent luthier operating at a reasonable price AND the guitar is worth a substantial amount, don't reset the neck just to sell it. If it's playable as is, list it and see what you can get for it. Just be honest about the condition. You don't have to tell potential buyers that "it needs a neck reset," but rather be very descriptive about the action, any belly bulge, saddle height, etc. Facts that matter. If you want to keep it for yourself and are concerned about playability, don't be concerned about the resale value. It'll hold if it's a valuable instrument. Just get it reset if you need to, keep it as-is if you're happy!