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When would be a time that I should try to get overcalls? If that isn't a time I should, when is? When I'm at higher limits?

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For instance I remember this from the small stakes holdem book: the board has 4 to a flush and you have a flush king high. A player bets out and you are second to act. If you raise now, you can get reraised and lose more bets to the ace high flush, or make others fold because of your raise. If you call you lose less when behind and make more when ahead encouraging other callers.

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This isn't quite the same thing. In your example, you're already behind. In this hand you have the nuts.

Any time there is two broadway cards on the board in a field this big, you can guarantee that someone has a straight draw. Make sure everyone pays the maximum to try to beat you.