Contextual note: The questioner is a 17-year old boy, writing on the last day of hol ha-mo’ed Sukkot (Hoshanah Rabbah)
Hi Rabbi Simon
With regard to shaving, I find it really uncomfortable to sleep with a few days to a week’s stubble and was wondering whether it would be permitted today as I regularly shave erev shabbat and yomtov.
If your circumstances are of genuine discomfort(מקום צער) it would seem that the rabbinic interdiction against shaving on Hol ha-Mo’ed (the intermediate days of the festival, ie Sukkot and Pesach) would not apply (ie, לא גזרו רבנן in such a case). We can also consider Rav Moshe Feinstein’s lenient view (Iggerot Moshe OH 1:163). There are also other respected authorities who take a lenient view, for one who shaves regularly. Nevertheless, I would not rely on those opinions were it not for the discomfort you describe.
Pitka tava and hag same’ah,
Rabbi Rashi Simon