Yes, automatics generally have a more constant state of wind if worn regularly, so this helps reduce the drift.
You could wind many times per day if you wanted, but with all the advances is design and materials, it's really not needed for the first 24 hours in order to meet the specs for the movement.
Omega allows more Delta (positional variation) at 24 hours than they do at full wind. So for example the 1861 at full wind is allowed to vary 15 seconds over the 3 positions measured at full wind (what happens in the other positions is a whole other discussion we'll set aside for now). 24 hours after full wind that Delta increases to 20 seconds over 3 positions. However If you wind your watch in the morning before putting it on, through the day the amplitude drop won't be huge due to the materials and design of a modern mainspring that gives more constant torque - the torque curve is fairly flat for the first 24 hours, and it's after that where things start to drop. So at 24 hours the timing is starting to drift, but that happens later in the 24 hours, so the proportion of the 24 hours it's running less accurately is relatively small, so the overall impact on daily rate is quite small.
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