Harrisal, there's obviously much debate out there about this matter. And like the choice of watch itself - it boils down to a personal preference. For me, after doing lots of research I've invested in a programmable watch winder. I am one to believe that watches simply can't be overwound - otherwise you'd see more watches break down from simple everyday usage on the wrist. A good programmable watchwinder has the benefit of stoping and starting regularly (thereby mimicing usage on a wrist) and some have a 'delayed start' allowing a watch to run down closer to the end of its reserve before starting the winding process.
All the technical benefits aside (which I've persuaded myself exist) - for me the biggest benefit of all is a simple one. And that is I get to see my collection displayed in front of my eyes. These timepieces after all, are items of beauty that should be seen and appreciated (if not necessarily worn everyday) - and there's something mesmerising about seeing them spin round and round and round...
regards,
vinhthang