Personally, I have:
Chosen to both takeoff and land with a tailwind worthy of consideration. In some cases, because the slope of the runway or local terrain made it a better choice, and, sometimes, not to look directly into the sun during the takeoff or landing.
Chosen to takeoff in a gusting crosswind when into the wind was a possibility - because of the large hill on the shore. I both did not want to take off toward rising ground, nor fly into what I anticipated could be settling air off the hill.
Chosen to land on the ice of a frozen lake: Amphibian (instead of the airport) - because I had one set of wheels up, and the other side down - 'done that twice. Straight floatplane (instead of open water), 'cause I had a broken cross bracing wire, and I was afraid that the other might break, and the plane flop into the lake. If it flopped on the ice, it would not sink (well, right away, anyway). It did not flop.
Chosen to land crosswind on the grass, rather than into the wind on the paved runway - I suspected, and later confirmed, a wheel was jammed. The tire slid on the grass, rather than burned on the pavement.
Chosen the unfavourable crosswind on the runway - amphibian - flat brake on one side, I wanted to be able to hold it straight with the remaining downwind brake. Landing was no problem, taxiing in - problem.
Chosen to complete a forced landing on a lake - the engine had stopped momentarily (unported fuel tank in steep turn), and I was not sure that it would stay running in the immediate, if I chose to go around at low altitude instead.
Flown ('cause there was no choice) a curved final approach and departure at a certified airport - 'cause there are mountains just off both ends of the runway there.
Announced to ATC that I did not know where I was (a couple of times

Taken off without planning to, with full flaps out, and with no seatbelt on - 'cause the person I trust, who was marshalling me while I taxied on a frozen lake, assessed that if I stopped, the plane might break through the ice. Happily, obstacles were not a concern, just getting the weight off the wheels was!
Prebriefed myself that in the case of an engine failure (Navajo) that I would gently close the other throttle, and land ahead as best I could, instead of trying to climb away on one - test flight on a modification, and single engine handling and speeds not yet known.
Prebriefed myself that I would land the plane on the belly (gear up) if a forced landing were necessary - frequently, when flying over an unsuitable wheels down landing surface. 'Never had to do it...
Just some examples which came to mind while I was mowing the runway this morning. I remind myself to get as many facts as I can about a pilot's decision, before passing judgement, because the pilot might have known something about the situation that is not [yet] obvious to those who might comment....