Replacing iTunes content with iTunes Plus

I see on my iTunes account that I have many songs I purchased prior to DRM-free content, and these "upgradable" songs number about 300. This might make things easier, but when I purchase the "upgraded" version, will the new version of the song also appear in the playlists that the original version was placed in? Or will I have to manually put the new iTunes Plus version back into the playlists? That might not be worth the cost to upgrade if I have to go back and replace each song in every playlist that it appears in. 

Your upgraded iTunes Plus music will replace the original purchases in your library. You will be given an option to delete the original files or move them to your desktop at time of download.  However, in my experience, the new versions don't always make it to my playlists.
Here is the iTunes Plus FAQ:  http://support.apple.com/kb/HT1711

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