weird ipod problem with manually syncing...help!

[senn246]

ok so seeing how i have more music in my library then my ipod can hold, and i dont want to check and uncheck every other song i decided to manually sync it but now i have some problems. keep in mind that when i say my ipod library i am viewing all the music from iTunes. Sorry for the lenghty post but i cant figure it out

First Question
i like to monitor my play counts but when i plug my ipod back into my computer it doesnt transer my ipod plays to my library plays, so its like i have 2 seperate play counts going on the same song, for example in my itunes library it says that "call and answer" has 5 playcounts, but when i look on my ipod it says 8 playcounts, but yet when my roomate did this and he plugged his ipod in, it combined his playcounts...we both manually sync our ipods but why does his combine the ipod count with his library counts and mine does not?

Second Question
i created several playlists on my itunes library and i wanted them on my ipod so i dragged the list into the ipod but when it start syncing the list it said that there is not enough room to put the playlist on, but i've always understood that playlists barely take up any room and since i have 3 gb left on my ipod so why does it say this? after it said this it said that it would sync as many songs as possible and it only put half onto the playlist. but now when i went back into my ipod library all the songs that were on the list became duplicates...so instead of it just making the playlist it re-added all the songs to my ipod. I asked a couple people and they said that the songs in my playlist werent already on my ipod...but they are. Taking "call and answer" for example again, it was already on my ipod and it had 8 counts, and in my library it had 5...but when i synced a playlist with that song on it they both went into my ipod library...i had "call and answer" twice on it, and one had 8 plays and the other had 5....if this made any sense to you then please help, if your confused say whats confusing you and ill try and clarify.....Thanks!

[S2_Mac]

1) Getting metadata -- play count, played date, etc. -- to carry back to iTunes from manually managed iPods is always iffy. In your case, iTunes is p'bly seeing the iPod track and the iTunes track as two different tracks; see #2.

2) When you transfer a playlist to an iPod, you are also transferring whatever music the iPod doesn't have. In the example you gave, there was something different between the "Call and Answer" file on your iPod and the one in iTunes -- one had album art and one didn't, or the two files had different tags, or some other 'physical' difference.

3) Maybe it's time to try syncing Smart Playlists and/or Sync Selected Playlists (about halfway down the page of this iLounge article (http://www.ilounge.com/index.php/articles/comments/the-beginners-guide-to-filling-your-ipod/) is a brief intro to this). You can set up smart lists that will provide content to match (or at least come very close to) your iPod's capacity, or work from a stock set of regular playlists and one or two smart lists that add new or popular or overlooked content...and counts and dates ratings will stay synced.