Hi, hope some can make use of this tip! After the first time it's a sinch!

1.) This is how I started;
Select the entire iTunes library > get info > change My Rating to 1 star
(Note: if you have previously spent a lot of work rating songs, I would suggest that you sort all songs by "My Rating" in the column, select all songs with 0 stars > get info > change to 1, then 1 to 2, 2 to 3, etc...)

2.) Now create a Smart Playlist:

3.) Match (All) of the following conditions

4.) Genre or Artist > Is > (what ever you want)
Example: Genre > Is > Jazz

5.) Use the Plus sign to the right and add one additional condition

6.) My Rating > Is Greater Than > 1 Star

7.) Limit to (0) > Songs > Selected By (Highest Rating)

8.) Live Updating (On)

Thats all for the "Smart Playlist"

9.) Sync iPod

Now go use your iPod away from your computer, select the playlist you created. Listen, Hate that song! (Move to (0) stars > tap center button three times: 1st = Volume - 2nd = Playhead Insert - 3rd = Ratings Stars)
Listen More, Love this song! Make it 5 stars, it will now play amongst the first and most often!

Note: at the beginning I set all my songs with 2 stars, if then I later rated it with 1 star it would drop from the playlist, with 0 stars I knew it was ready for the trash! After changing all the ratings on the iPod, my experience is the next time you sync, it updates the ratings in iTunes!

Please use the poll, would like to know if anyone found this useful?