Some songs not synching

I subscribe to several podcasts featuring a song of the day. Because I want to listen to the songs with other music (e.g., in a playlist), I convert those podcasts to music by changing the Media Kind on the info screen. As far as I know, this doesn't violate any copyrights, rules, etc. Unfortunately, sometimes these songs won't synch with my iPod after they're converted, unless I change them to an Apple lossless version. This consumes more space than I would like. Any thoughts as to what might be happening?

Forget lossless, I doubt that podcasts require such quality. Try to convert them (Advanced>Create mp3 version) to mp3 or aac.
Go to "Edit-preference-general-import settings" and choose the sound quality that will satisfy you. 192 kbps is more than enough. Even 128 can be OK.
After conversion you can check Media kind, correct tags or join the track to any playlist - this is a normal song now.

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