So having more than one manual watch how do you handle the winding up? Do you wind them up daily or regularly and by doing that keep them "ready to wear" in the box or just wind them up and set the time when you wear them?
Yes. You’re absolutely right. Manual winding is supposed to run only if and when it’s on duty. Else it should rest in the box or drawer undisturbed. I prefer even my automatics too same way but some prefer them on the watch winders to be ready whenever needed. Engine should run only when needed...
I let 'em run down, for the same reason I will never use a watch winder for any of my automatics. If I need a watch to just grab and go, I'll pick a quartz or the mechanical that I was wearing yesterday and is thus still wound; if I want something else, then I'll go through the little ritual of winding and setting it before I strap it on. For me, that's part and parcel of the mechanical watch experience.