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In regards to the Find in Files function, is checking 'Regular Expressions' implicitly slower? I usually try to check/uncheck it to match my needs, but sometimes I forget. Is there a major speed issue with having this checked when I am looking for standard text? Can I just leave it checked with no issue, provided my term doesn't get tripped up?

Yes, regex searching is intrinsically slower than plain text searching. However, the decrease in speed is remarkably small, especially when considered against the increase in expressiveness. And if you haven't been able to determine the speed difference, it can't be an issue for you...