Greyed out circle, but I have enough memory?

Usually the circle means I didn't have enough memory, so I just clear out stuff I don't want and it's fine. However, I have 5.81GB free (according to the little bar at the bottom, but it's lied to me before)... I'm trying to put on one song, but it won't let me. I'm preeettttyyyyyyy sure this song is not over 5GB. I was actually trying to put the whole album on, but that didn't work, so I tried just one song... still didn't work. I'm backing up my iPod now, thinking of wiping it and putting everything back on... but that's such a hassle. I'd really love for iTunes to just work instead of messing up every single time I try to do anything. D:
I haven't updated iTunes recently, could that effect it? Why does that effect it? I'll just roll on the floor and sing to myself if it keeps giving me trouble bleh.

iTunes eventually updated after I did it manually. Songs still not syncing, though. I've updated and reinstalled iTunes, restarted all the little mobile device support things, ran diagnostics, renamed the sync folder, moved stuff around, changed it to the recommended file type, let iTunes put it in its own little music folder. Done everything but restore my iPod, but that always takes forever and a day... and I'm paranoid of losing stuff. I don't have access to my old music files right now so I don't wanna risk it.

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