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The phrase "a headache of difficulties" is correct and usable in written English.
It can be used to describe a situation that is causing significant stress or trouble due to multiple challenges or obstacles.
Example: "The project turned into a headache of difficulties, with delays, budget overruns, and team conflicts."
Alternatives: "a source of frustration" or "a burden of challenges".
Exact(1)
Somewhere on the edges you were, but we couldn't come together, and all was a headache of difficulties and distances.
Similar(59)
He had no fevers, no chills; just a headache and this difficulty breathing.
"She had a lot of difficulties".
"We faced a lot of difficulties.
Part of the reason is that scheduling American tours has become a bigger headache because of greater difficulties in procuring the necessary visas.
That had a level of difficulty, too.
Carefully note the onset of stroke symptoms (weakness or numbness on one side of the body, loss of vision, confusion, difficulty speaking, a headache like you never felt before).
It's a bit of a headache.
Yet this may present some difficulties in respect of Labour's financial relationship with affiliated unions – although for some in the party, it would not be so much of a headache.
She complained of a headache.
"Got a bit of a headache".
More suggestions(1)
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com