Not something I've experienced directly (never had an iPod big enough to sync my entire music library, lol) but twenty eight songs not transferring sounds like it could just be a couple of albums that have gone awry; were these ripped from CDs or bought through iTune Store? Also, do all the songs play OK in iTunes? Might be worth spending a few minutes scrolling through iTunes to make sure all the files are accessible i.e. no little "!" alongside any of the tracks.
If the songs were bought from iTunes Store, then were they bought under the same account that you're currently logged in as? That might prevent them playing, which would probably prevent them from being transferred??
Not sure that there's any real shortcut to finding which songs are missing - but finding two albums out of two hundred sounds like a better starting point than trying to find twenty songs out of two thousand
Good luck, Pete.