How to sync iPod without losing music? (Lost external hard drive, which I used as a source)

I stored my iTunes library on my external hard drive, which held music purchased through iTunes, other sources, and personal music files.
My external hard drive recently broke. I will have to rebuild my library, but I have some things I'd like to add to my iPod. If I sync it now (the songs still show up in my library on iTunes, but there are no files to support them), will I lose all those? Previously, there have been times where I synced my iPod without my external hard drive and it kept them as long as I didn't delete them from the library or uncheck them. The only thing was that if I did remove them, I wouldn't be able to put them back. Does it still work like that?
I'd rather not risk all my music to put 4 songs on, if it won't work, you know?

Try syncing using the manual method
Try syncing using the manual method
Managing content manually on iPhone, iPad, and iPod
However, the rebuilding you did may have resulted in the iPod seeing the library as a new library. You can only sync with one library/computer. In that case:
Syncing to a "New" Computer or replacing a "crashed" Hard Drive: Apple Support Communities

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edited.

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