I suspect there is a little problem in Italian hyphenation. With expression like "quell'impossibilità" (with an apostroph) the possible points should be "quel-l'im-pos-si-bi-li-tà", but Prince seems to recognise only the first point "quel-l'impossibilità". If it is so, I think it should be corrected, Italian abounds in long words and in such cases the effect can be rather unpleasant.
Forum › Bugs
Little problem in Italian hyphenation?
Fourteen years ago (time passess...) I found a similar problem in Lout. I don't know if this is relevant, but anyway this was my solution:
https://lists.gnu.org/archive/html/lout-users/2001-09/msg00068.html
https://lists.gnu.org/archive/html/lout-users/2001-09/msg00068.html
Update: I checked with "hyphens: prince-expand-all" (I have discovered just now that option) and I can confirm: hyphenation points after the apostroph are not recognised (neither in Italian nor in French).
Update 2: Prince uses the version 4.8 of Italian TeX patterns; the most recent is 4.9 but that has (unfortunately...) no relationship with the problem.