This has been asked before (here and here), but there is no complete answer. So I want to address this question once more.
Each skill has a finite amount of exercises. If a student will work on one skill for a long time, exercise will start to repeat. So he may try to remeber the answers. Is this plausible issue?
This question is mostly for teacher who have been using KA for long time and might have encountered similar issue.
I've used Khan Academy as a coach for hundreds of students -- and you're correct. Especially for multiple choice questions, students will start to remember answers, and that's too bad.
The ideal scenario would be procedurally-generated questions -- where a program would randomly generate the question so that it was different every time. Even for word problems, it would be possible to constrain the randomness so that the problem is reasonable and solvable. The real problem comes from the hints that Khan Academy provides -- those would need to be specific to a randomly-generated problem, which I think would be much more difficult to program.
The alternative would be just to greatly increase the number of possible problems. In some cases, there are as few as 20 separate problems; I think you'd want to have at least 100 to prevent memorization from becoming a factor. But I just don't think that's a top priority for the programmers right now.
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