In a database, when should you store derived data?

My question is about denormalization. In a database, when should you store derived data in its own column, rather than calculating it every time you need it?

For example, say you have Users who get Upvotes for their Questions. You display a User's reputation on their profile. When a User is Upvoted, should you increment their reputation, or should you calculate it when you retrieve their profile:

SELECT User.id, COUNT(*) AS reputation FROM User
LEFT JOIN Question
  ON Question.User_id = User.id
LEFT JOIN Upvote
  ON Upvote.Question_id = Question.id
GROUP BY User.id

How processor intensive does the query to get a User's reputation have to be before it would be worthwhile to keep track of it incrementally with its own column?

To continue our example, suppose an Upvote has a weight that depends on how many Upvotes (not how much reputation) the User who cast it has. The query to retrieve their reputation suddenly explodes:

SELECT
  User.id AS User_id,
  SUM(UpvoteWeight.weight) AS reputation
FROM User
LEFT JOIN Question
  ON User.id = Question.User_id
LEFT JOIN (
  SELECT
    Upvote.Question_id,
    COUNT(Upvote2.id)+1 AS weight
  FROM Upvote
  LEFT JOIN User
    ON Upvote.User_id = User.id
  LEFT JOIN Question
    ON User.id = Question.User_id
  LEFT JOIN Upvote AS Upvote2
    ON
      Question.id = Upvote2.Question_id
      AND Upvote2.date < Upvote.date
  GROUP BY Upvote.id
) AS UpvoteWeight ON Question.id = UpvoteWeight.Question_id
GROUP BY User.id

This is far out of proportion with the difficulty of an incremental solution. When would normalization be worth it, and when do the benefits of normalization lose to the benefits of denormalization (in this case query difficulty and/or performance)?