IPod not playing re-ripped tunes with higher bit-rates

Since I got my iPod and have more storage I have been slowly re-ripping some of some tunes at a higher bit rate. iTunes doesn't appear to try to sync these songs and re-upload them to the iPod.
What happens is that the song stops playing part-way through the song. My guess is that it is due to the file size of the old (lower) bit-rate, as if it still thinks the EOF is at the same spot even though the file is now larger. It's almost as if the index doesn't get updated properly somehow.
I've tried deleting all the songs on the iPod and even doing a restore, but that doesn't always fix it. Some songs do it, some don't.
I know the rips are good because I can play them all the way through with either iTunes or Media Player.
Any help on getting it to sync them properly?

I assume that I have to re-rip the songs at the higher bit rate, unless there is Is there an easy way to do that without re-ripping them. 
Assuming you want the higher audio quality (and not just a puffed up version of the same low quality track) you will have to re-rip from the CDs.
Also, what happens to the lower bit rate songs in my playlists, especially if I delete the lower bit rate versions from my library?
Under certain conditions, iTunes will recognize the CD and ask you if you want to replace the existing versions.  Say yes, and the rip process will automatically do the replace.
In case it does not ask, just go ahead and rip, and then do the replacements manually.

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