If a person stays up the whole night, he must be very very careful to daven properly, with proper kavanah, and without drowsing. ESPECIALLY during k’ri’as sh’ma and Hallel, where one missed word invalidates his fulfillment of the mitzvah. (In Hallel, it also creates a berachah levatalah). Consider going to bed at alos hashachar (the night is then over) for a few hours, and davening at a later hour.
But this is only muttar if arrangements have been made for someone to wake him in time for his davening. This requirement becomes necessary at a half-hour before alos (but it is not necessary if he goes to sleep before that).
If one forgets to say ya’aleh v’yavo at Minchah Friday Rosh Chodesh, and Shabbos is NOT Rosh Chodesh, it is a major shayloh if one can daven ma’ariv twice.Such a case (where you will not be saying yaaleh veyavo at the make-up tefillah) is a general shayloh even if it occurs during weekdays, and the aytzah given is to daven the second Tefilla as a nedava, which cannot be done on Shabbos!
MB says one Maariv only.
Aruch HaShulchan is noteh –two.
Rav Malinowitz says: DON’T FORGET YA’ALEH V’YAVO AT MINCHA!!