It has a 60-hour power reserve. That doesn't mean it will run for 60 hours after you take it off. It just means it's capable of doing so. Depending on how active your lifestyle is, it may stay fully topped off, or it may hover with only a few hours of power reserve after removing the watch. Because of that variability, no one can say how often you'll need to keep it wound up. You'll discover that over time, and it's not a big deal to reset when you need to.
You cannot overwind this movement. Almost all modern watches have a clutch that will slip to prevent overwinding.
My opinion would be to not bother winding just to keep it going. If it dies, it dies. You'll need to wind it at that point anyway, and it doesn't hurt the watch at all. The benefit is that your watch will tell you exactly when it died, so you'll come to learn just how much of a power reserve you typically keep on the watch.
I would recommend going to YouTube and typing in "Omega 9300" and watch a review from WatchBox. Tim Mosso gives excellent, straightforward reviews/descriptions of watches. He describes operation, specs, etc very well.