Winding and setting the time
To wind a manual watch, simply rotate the crown clockwise until you feel some resistance, then stop (for a stopped watch, this will generally be in a range of 25-30 turns of the crown). Automatic watches (which wind themselves as you wear them) may require just a bit of winding to get started. They won’t provide the feedback when fully wound, however.
From our completely unscientific survey, we found that both watchmakers, as well as the rest of us, are split as to whether they turn the crown of the watch in one direction only to wind, briefly releasing between each motion, versus holding on to the crown the entire time while winding, moving back and forth in both directions. We haven’t found an example of a watch with wear due to the rocking back and forth while winding, but in theory there can me some minimal amount, so if you reeeeally care about the fringes and you “merely look after [the watch] for the next generation” ™, then maybe just one direction is for you.
For setting the time, always advance time forward, with the exception of small movements when setting the precise time. Be aware that there are watches with complications that you do not want to adjust during certain periods during the day (really during the evening period around midnight related to date changes). For those we generally stay away from making adjustments during a wide range of time, say 9PM – 3AM.
A bonus note: not all watches set by winding the crown in the same direction! Most of mine, for example, set by turning the crown clockwise, but others to set counter-clockwise (I didn’t learn this until I had made a handful of purchases).
Some chronograph owners leave the movement running all the time. This likely results in negligible additional wear on components, but will reduce the power reserve (how long the watch can run without being wound) and result in more frequent servicing required.
Watch winders
Watch winders are not a necessity, they are more for practicality – either so you don’t have to wind them, or that you have an automatic perpetual calendar watch where it is a PITA to set the date (if no quick set). If you do want a winder, consider a model that can be adjusted, and keeps the same amount of wind in the spring as when you put the watch in the winder.
We haven’t seen examples of additional wear on a watch from a winder versus manually winding. Our personal opinion, based on nothing, is that it is just as good, or better, to leave the watch unwound until we want to use it. There should not be any issue with letting the oils sit…and if there in an issue, by that time our watch is probably due for a service. And yes, we enjoy winding our watches ☺ For those watches that we rarely wear, we pull them out and wind them every few months.