I can feel your pain as I went through it myself at the start of using ZumoCast...
The problem is not on your iPad (nor is it with ZumoCast). It's how your folders are identified for ZumoCast to use from/on your PC or Mac.
The best suggestion I have for you (I've had to do it myself): Pick one of the songs that you cannot play on the iPad via ZumoCast. Go to your iTunes and find the actual address where that song is. The odds are pretty good that the song is in a folder you have not set for ZumoCast. Use ZumoCast to set preferences for that folder and then it should work fine.
iTunes has a very, um ... interesting way of file management, especially for music. If the MP3 [for example] is not IN the iTunes folder, iTunes will map a way to it. This way, it'll play the song from that location, but it'll still be IN that location. Your playlists also map to other places on your PC if they aren't in the iTunes folder. ZumoCast's "problem" with using your playlists is that it can't (doesn't?) follow the link. So, it says your song's not there ... until/unless you add that end folder into ZumoCast via the preferences.
There, that's clear as mud, eh? Ah heck, just do what I did! Buy an entire NEW desktop PC and when you put all your songs back on it - ensure they all go to the iTunes folder (and that the default is to put ALL new songs added to iTunes into THAT folder). Easy-peasy, problem solved!
Hope this helped a bit (well, except that last paragraph...!).
Marilyn
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