I generally don't give up on a stand location until I've gone a few seasons without sighting anything. If a given venue is unproductive, I'll just let it go for the year and come back the next. Most of the venues we've given up on were ones that we tried early on, but turned out to be zilches. The majority of the venues have been in place for a decade or two.
What makes them unproductive? Generally speaking, two mature bucks are on the property at any given time. They move off and go somewhere else during the rut and what we see during season are several other bucks that have gone roaming themselves. What's stable are the doe herds. We make them happy and they stick around and act as bait. If the matriarch of one of those herds gets a bone up her butt about a stand, the other deer will avoid it like it was poison. This behavior will last multiple seasons. In the worst case, the curse was permanent. We set up a stand within sight of the old site, and could see deer avoiding the cursed tree for a decade. My sons are now using the new site, and our new guy, Foxtrot Charlie got a doe out of it this past season.
On the other hand, I've seen two instances where solitary doe have ID'd a stand and come every time I was out. They learned to bring pesky bucks by the stand. This behavior lasted a couple of seasons each time.
What makes me bail for a season? If I've had a few sits at a venue when I knew it should have been productive and wasn't, I'll bail for the year and hunt somewhere else. If that goes on for a few seasons, I'll seriously start to question the sense of maintaining the venue.
