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The part of the sentence "hard to know when" is correct and usable in written English.
You can use it to express difficulty in determining when something may happen. For example: "It can be hard to know when the right time is to make a move."
Exact(60)
It's hard to know when you become a 'proper' adult.
"It's hard to know when the hammer will come down".
It's hard to know when to hit each one".
It's hard to know when that will be.
It's very hard to know when it's time to stop dreaming.
"Without accurate forecasts it is hard to know when to pull that trigger," he said.
It's hard to know when, if ever, Congress will be half-female.
"It's hard to know when people will tire of it," Knutsson says.
It can be hard to know when Christmas starts these days.
Locally franchised operations tend to be worse, but it's hard to know when booking.
As Fry explains, it was hard to know when a song was completed.
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Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com