IPhone 5 refuses to sync most of my music for no apparent reason

iPhone 5 running the latest version of iOS 7, trying to sync to the latest version of iTunes for Windows. Syncs about a third to half of my music (700-1200 songs out of 3000) before saying "finishing sync" and displaying nothing more than the Apple logo at the top. Bar at the bottom displays the 20 gigs of music that would be, but upon looking at my phone I have access to maybe a handful of tracks, ranging from 50-100. Have tried a system restore, have tried unchecking all music and rechecking it. Most of this music is in high-bitrate MP3 format, some is on .aac, none of it is "protected" or purchased from the iTunes store. This music is on an external hard drive along with my library file; going to try to move them to my internal later today, as I fear my hard drive might be dying and this might be causing the problem. If there are any utilities that give me more feedback than what iTunes is currently giving me, I would appreciate links to them. This is by far the most frustrating issue I have ever encountered as a tech user and the lack of transparency as to what is actually occurring when I plug my iPhone in contributes much to that.

If the hard drive that crashed is the one that stored the itunes library, be sure to restore the library from Time Machine (mac) or whatever backup you use on windows.  That will get back your music.  I suspect that the replacement drive has an empty itunes library and thus, perhaps, the itunes match used that to sync to its servers.
Try posting in the iTunes Match forum, you'll probably find more knowledgeable folks there.
https://discussions.apple.com/community/itunes/itunes_match

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