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"Set the threshold to 12PM if the 11:05 flight is OK with you"But the 11:55am flight is not OK. In any case, this is breaking what users have to do now - they have to purposely break the UI to get the results they need. They have to lie to the system to coerce out the answers they actually want, as opposed to the system being smart about it.
When I say "leave at 11am", I mean "the closer to 11 the better", not "place a hard limit".
Not to mention, Kayak's results display is terrible - the information is densely packed and not in an easily parseable way, making flight comparisons a gigantic chore. If I want to compare my departure times, it stuffs the return trip (which frankly, has no business being there) times right underneath.
It also insists on showing raw time values, without any visual indication of longer flights vs. shorter flights, nor visual indication that differentiates departure/landing times. This is only a couple notches above comparing UNIX timestamps. Manually, consciously subtracting time values is not something people are good at, and certainly humans perform poorly at it when forced to do it many times in short order.
It is, in short, needlessly precise. It doesn't matter if one flight leaves at 6:05am and the other leaves at 6:08am. I don't need that kind of precision in my decision-making process. Nor do I need to know if one flight is 8 minutes longer than the other. It's noise, and it's poor UX.
Nowadays I go out of my way to avoid Kayak - or really anyone who fails to separate the two legs of a trip. It's ugly, it's information overload, and it's downright maddening.