6gen nano doesn't like certain songs

There seems to be a problem with certain songs on my dad's 6gen nano.
It plays with no problem but on certain songs it will play for about a minute, makes a "bubbling" noise then skips to another song.
Can anyone help - what am I missing??
Thanks

OK, this reply was nice. It helps with one question. Also, I have discovered that the Nano does not register songs/podcasts as "played" unless it is syncing songs or podcasts. I now have Podcasts set to sync the latest episode and this eliminates the blue "unplayed" ball when I reconnect the Nano.
Now, how do I fill the rest of the space with music? I tried "Manually Manage Music" and this way I can fill the rest of the space with some of my music. But I'm stuck with figuring out how to Randomize the fill. I put the songs in alhpabetical order by title and then stick in the first 200, then the second 200 after a few days and so on. Not very satisfying.
I tried to sync the music by checking the box but it won't select any music on it's own. Just tells me that there is no more space on the iPod and I believe it just starts at the top of my playlist and works it's way down, always the same songs. I know how dumb I am for not being able to figure this out but, again, an Autofill button would be the cat's meow for my situation. I used to Autofill my Shuffle and then delete as many songs as necessary to fit the podcasts I needed for any given day, the exact opposite of what I'm doing now and much more satisfying. Does anybody have a cool way of doing something similar?
TIA, Rick

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