Is it correct to use "to do" twice in a sentence? For example: is it correct to say "how to do that and when to do that is a problem" or should it be "how to do that and when doing that is a problem"?
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1If you want to combine them, you could write how and when to do that is a problem. – Barmar May 01 '15 at 22:53
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Since How to do that and when to do that are simply nounal phrases, there is no harm in using them multiple times in the same sentence.
Indeed you could say How to do it, when to do it, and in what manner to do it, each present problems.
Your alternative sentence does not make grammatical nor idiomatic sense
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