It's is one of the [Niju kun](https://en.wikipedia.org/wiki/Niju_kun) of
Funakoshi, the meaning seems quite "cryptical" to me, also seeing the english
and italian translation.

The italian translation is something like "be always creative", and the
english is "Be constantly mindful, diligent, and resourceful, in your pursuit
of the Way". Not sure why this difference!

Which is a proper translation, or the meaning of the kanji?

I don't know any japanese but I tried, without success, to figure out
something with google translate.
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question
translation
How would you translate 常に思念工夫せよ?
* 常に: _tsune ni_ , 'always'
  * 思念: _shinen_ , 'to think deeply', in this context
  * 工夫: _kufū_ , 'to seek for the better', 'to try to come up with a new idea', 'to exercise ingenuity', etc.
  * せよ: _seyo_ , 'Do' (archaic imperative form of する)

So this short sentence just says "Keep on thinking, and seek a new way". The
translation in the English Wikipedia article has several phrases not included
in the original sentence. Your "Italian translation" is a bit too short,
though.

(Note: I don't feel this 工夫 particularly refers to some difficult Zen/Buddhism
related concepts.)
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answer