Ipad Remote app works for only half the songs in my iTunes library, and sound still comes out of my Mac instead of my iPad.

Can anyone offer suggestions? I realize there are two separate issues here.
1. I thought I successfully connected my iPad with the iTunes library on my Mac/ Hard Drive via the Remote app. However, more than half the songs in my music library will not play on the Ipad; when I click on any one of them using the iPad's Remote app & iTunes, I get a message box that says: "An unknown error occurred. Please check your library and try again." These songs all play fine through my Mac's Itunes program.
2. I had thought I could use the Remote app to get my library "into" my receiver, connecting the iPad to the receiver with an RCA-to-headphone adapter. This adapter works great to play music that "lives" on an iPod or iPad. But it does not seem to be able to access music that the ipad is controlling only remotely. If this is true I will be pretty unhappy...

Thank you. My two questions have now shifted.
1. You are right-- I have been unsure as to whether Homesharing or Remote was my answer, and I did set up Homesharing on both my Mac and iPad. It still appears that my music comes out of the Mac, only. How can i use Homesharing to allow the iPad to play music?
2. And I went back to check again, and saw that somehow, the songs that my iPad cannot locate are also somehow missing now on the Mac, even though they used to be accessible. My entire music library is stored on an external hard drive, which I used to connect to my Mac with USB. I just got a new router and now have the music hard drive connected via USB to IT instead of the Mac. I would bet that this is why so much of my library is no longer accessible-- I must have used different settings to save some of my songs, and the hard drive's new location shows that. Can anyone help me make my entire music library playable ? Thanks again

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Thanks for using Apple Support Communities.
I would go ahead and make sure you can first download the content, then remove the song from your iTunes Library, and download again from your iTunes past purchases. The article below will walk you through the entire process:
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http://support.apple.com/kb/ht2519
Take care,
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tt2

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http://support.apple.com/kb/HT1391
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http://support.apple.com/kb/PH12491
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Ipad Remote app works for only half the songs in my iTunes library, and sound still comes out of my Mac instead of my iPad.

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