Removing duplicates from playlists and keeping ratings.

When I first started using iTunes, I thought it was a great program. However, once my music collection outgrew the size of my iPod, I began to see it has many frustrating limits and annoyances. I would appreciate it if anyone could help me resolve the issues I'm having. If anyone from Apple reads this post, please pass this on to your software developers because I know there are tons of people having the same issues I am having (just do a Google search if you don't believe me).
1) My first method of managing my collection is to only put the files I want on my iPod in my library...this way I know exactly what's on my iPod. However, I found that in doing this, the ratings I created on my iPod were not reflected in my library on my computer. Is there any way around this? Also, I've noticed that if I remove a file from my library, I also lose its rating. I know that the rating can be stored into the id3 tag. Why is this not done??? Is there anyway around this?
2) My next method was to have iTunes automatically update my iPod from a playlist I created (the playlist had no meaning other than it was where I put all of the music I wanted on my iPod). But I soon noticed that iTunes wasn't smart enough to realize that there were duplicates (sometimes 5 copies of the same song). Which is what happens when you don't feel like taking the time to see if you've already added your favorite Alice in Chains album, so you just drag-and-drop it again. The library is smart enough to handle this (i.e., if you drag the same folder into the library twice it only adds it the first time and it ignores it the second)...why can't playlists do the same?
I would appreciate any feedback on my issues. Thanks in advance!!!
Josh

Depends on Why duplicates are happening. If you are adding the same file again then iTunes will make another entry. If you have the same track in different formats it may show up again with same track name.

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