It is not recommend to adjust the date on your watch between the hours of 8pm and 1am. Whoa! Blown away. They don't teach you this in home ec.
Umm more like 10 and 2... but in all honesty it really depends on the movement. Some there is no issue esp modern movements. Some older ones the window is larger like 9 and 3.
On some watches (omega cal 564) you should change the time till the date ticks over (so just past midnight) and then change the date...according to my omega certified watchmaker this is due to the particular date change mechanism (which is a pulling out, pushing in of the crown) on that particular movement. There is no ‘one rule for all’.
Most of the time I don't know whether my watch stopped in the AM or the PM, so I have to do it this way - time first, then date.
That only makes sense if it’s a cal564 (I beleive) which has the strange crown-popping date advance feature...
I have a 1967 564 - amazing movement. If I jump up and down near the watch it seems to be enough to set it ticking from an empty main spring. Pumping to set the date did take some getting used to / I still have a fear I might pull the stem out (I had a bad experience with an old 30t2 movement once)... I can be a bit heavy handed :0)