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Basically he's a scientist who knows too much about his world.
I think that Sans knows when you reset, but he doesn't know what you did before you reset.
For example, you can do a Pacifist Route, and then reset during it.
Sans would not know that you were on a Pacifist Route, he'd just know that you reset.
Well, that's what I think. :P
Somehow he's got photos from alternate timelines, including the group photo from the pacifist ending.
Which means that he's aware of what you've done in the other timelines, and therefore he can easily deduce what you're trying to achieve in the current one.
As an example, he knows that you've killed Toriel in some timelines, and spared her in others. Toriel is both alive and dead -- in separate timelines that are equally real. That's quantum mechanics, similar to the Schrödinger's cat paradox.
He definetely doesn't keep memories from other timelines.
In Pacifist Ending he needs to send himself a secret password through you to believe you're a time traveller.
In Genocide battle it seems he didn't know you were the anomaly at first.
Flowey in Genocide talks about having messed with Sans in the "past" and yet in all paths Sans ramains oblivous to Flowey's existence.
Whatever he knows seems to come from his research, not an actual first hand experience. Where exactly does he talk about Toriel, i can't remember it.
The game hints that Sans is from a different universe/timeline and that’s how he knows about determination and resets. The riverperson quote, “Beware of the man from the other world,” also is likely to refer to Sans.