I have an old iPod, first generation. I want to play a friend's music thru my Bose radio. I've emptied my iPod to my itunes library to allow space on the iPod. Question is: Can my friend put his music on a flash drive and somehow transfer to my computer.

I have an old iPod. First generation. I want to play a friend's music thru my Bose radio at an upcoming party.   (already use my Pod w/the radio). Ive emptied my iPod to my itunes library to make more room for additional music.
Question: Can I somehow download my friend's playlist - which is on a flashdrive, transfer it to my itunes and then transfer to the iPod??

If the Apple Store Genuis says you can't sync music from an audio CD to your iPod (because it's too old), he or she is not much of a "genius." 
That question is not even related to your iPod.  First step is to "rip" the music CD into your iTunes library.  Once the songs on the CD are in your iTunes library, they are like any other songs in your library, and you can sync them to your iPod as desired.  This article seems to do a good job of describing how to rip CDs
http://www.macworld.com/article/1156861/howto_rip_cds.html
NOTE:  When you insert a music CD, it appears in the iTunes sidebar, under DEVICES.  If you do not see the sidebar (along left side of window), from the iTunes menu bar, under View, select Show Sidebar.
It was the context of your original question, not the actual task.  You can easily add songs files that are on a flash drive to your iTunes library.  Open a window that shows the flash drive contents.  Drag the song files from that window to the iTunes window, and drop them on your iTunes Music library.  Or, use the command
iTunes menu bar -> File -> Add to Library...
NOTE:  Open your iTunes preferences, Advanced tab.  If the checkbox for Copy files to iTunes Media folder when adding to library is NOT checked, those songs from the flash drive will only be accessible (for playing and syncing) when the flash drive is connected.

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