Winding a vintage Rolex is a delicate process. Too much winding causes wear and tear, too little and your watch won't run properly. So how much should you wind your Rolex?
My personal rule of thumb is to wind the watch until it starts running again. You shouldn't have to force it. If you feel grinding, that may be a sign to have your watch serviced.
If you're not sure, err on the side of caution and wind it a little less rather than a little more. Most newer Rolexes will have a power reserve of around 48 hours and the older ones less.
With a bit of practice, you'll quickly get a feel for how much winding your Rolex needs. Just remember to take it slow and be careful not to overdo it.