Orzeszek Ratings is free software to synchronize play counts and ratings between iTunes and Windows Media Player. If you are planning to manage your music collection on a single computer with the help of iTunes and Windows Media Player, Orzeszek Ratings is the best solution. This software can effectively sync both the play counts and the ratings. It does not works with iTunes alternatives, though.
However, this syncing of play counts and the ratings is possible only if the file in question is common to both Windows Media Player and iTunes Library. It should be kept in mind that the files should be shared by both iTunes and Windows Media Player to make this work. If there are two files kept in two separate folders this syncing will make no sense. You should also realize the fact that converted files won’t be synced. Which means the WMA files you added to the iTunes library won’t be synced given the fact that iTunes and Windows Media Player are not addressing the same file again.
Moreover, there is an issue with the star rating. iTunes supports half star rating whereas Windows Media Player does not. In this scenario converting the stars from iTunes to Windows Media Player is bit of a problem. They have found the solution in the form of rounding off the half rating value to the nearest full value. Also check out software to add lyrics to Windows Media Player.
In this scenario Orzeszek Ratings is a fantastic solution.