This is one of the reason why I look for long power reserves on my watches. They would never have to stop working and I'd never have to worry about getting a watch winder. I can tolerate accuracy say until +6 to +8 sec per day, that would mean a maximum 8 minutes ahead every 2 months, the time you need to adjust the calender from 31 to 1 on a 30 days month. That works out to be at least 6 or 7 times a year. However, due to travelling and different time zones, I'll end up adjusting it more than that.
The one watch that I had adjust the most frequent is my hand-wound moon-phase watch. I'll normally let it run down right on the new moon or full moon day and wait till the next cycle 29.5 days until I wind it up again to wear it, to save the trouble of adjusting the moon phase to the correct day.