Quick Question About Repeating Songs Within A Playlist

Here's the situation: I have 45 songs in one playlist and would like to hear 5 of the 45 songs being played more often than the other 40 songs. Is there a way for me to do that? I tried rating the songs, but it repeated ALL of the songs and not the 5 songs I wish.
Thanks for your time in advance.

At one point, I think, desktop iTunes used to have a checkbox for playing higher-rated songs more often when in shuffle mode, but can't find it now. I don't think that ever existed on iOS devices.
You could make a request for such function here:
http://www.apple.com/feedback/

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It sounds like your issue here is that iTunes can not find the files for some of the songs you have brought into it. This happens occasionally even if the songs have not been moved from the location that iTunes places them on import or purchase. When you try to use the song, iTunes prompts you to find the file, as you have seen.
To find the file, use the information in this article to navigate through the iTunes media folders -
Locate and organize your iTunes files
If you are still unable to locate the files, you may need to download them from the iTunes store again, or rip them from your CDs. See this article for assistance with downloading your past purchases -
Download past purchases
Thanks for using Apple Support Communities.
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Are you automatically updating your iPod?
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Quick Question About Repeating Songs Within A Playlist

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