Grayed Out Song (When Sync'd to iPod)

A few days ago I bought a few songs on iTunes. Once finished I sync'd up my ipod touch and later on I listened to them from my ipod. However, I noticed that one of them sync'd twice onto my ipod, so I just deleted on of the copies and thought nothing of it. About two days later after I had made some purchases on my ipod, I sync'd my ipod to the same computer from before just to update my computer's library. When I finished, the song that was previously doubled upon syncing a few days earlier was no longer on my ipod. I looked and the song is still in my library. I then tried resyncing a few times and also taking off all my music and syncing just the particular song, but to no avail. When I resync'd all my music, I looked at the library of music on my ipod and I see the particular song there, but it has a gray exclamation point next to it. When I right click I am unavailible to find an error message or number. Normally I know this problem to occur when itunes cant find the origin, but I know that the song is on my computer, and it certainly plays on itunes just fine, it just seems not to want to sync to my ipod. When I compare the song in question to the other song I bought with it, there seem to be no differences in bit rate/sample rate either
tl;dr- song on my computer but won't sync to ipod touch.
I will note that I'm using a 1st gen ipod touch (ios 5.1.1) (32gb) and the hold button no longer works, but otherwise I haven't had other problems ever with my lovely machine

Trying to resolve the coverflow crash (crashing Music app, crashing the iPod) even when no music is playing, I finally told iTunes to not sync music and sync'd the iPod Touch 4th Gen, erasing all music from it. Then told iTunes to sync all the music and let the iPod Touch resync.
This resync did solve the problem of the blank Genius playlist.
This resync did not solve the coverflow crash problems, however.
See https://discussions.apple.com/message/17045668#17045668

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