Answers:
IF you are referring to LOCATION, you shouldn't use the word TIME at all. Time does not happen "where;" time happens "when."
Time refers to "WHEN." There are many times WHEN I have made mistakes.
WHERE refers to location: There are many corners where I turned left instead of right.
If you are referring to an incident repeated x# of times, you should use the phrase "times when" because you are referring to time.
Depends what you are talking about. 'When' relates to time and 'where' relates to place so you could say
There have been many times when I have regretted some of the things I have done.
There have been many times where I could have made a difference.
It all depends on what the end of the sentence will be. If you are asking just based on what you have posted then I would have to say the correct answer would be "there have been many times when" since a time is a when.
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