How do I get purchased and ripped music from my iPhone to iTunes when it won't sync the traditional ways Okay, so I have a BUNCH of music on my old iPhone and my best friend wants to convince her mom to let her have it.  First, I want the music off it, because they're my favorite artist.  Also randomly I got a bunch of other songs my mom downloaded for me, and I really want those too.

Here's my issue.  Most of the songs were either on the phone before I got, or I ripped some CDs.  Now I've done this before, but with when I went to sync my music.  It said 0 songs.  I have over two hundred songs. I'd like to add that when you go to your music, or at least when I did before my last computer crashed that had all my music from iTunes, plus over 600 more, it pulls up all your music to sync.  

When I tried to back up my phone to hopefully get it that way, it made me authorize my computer almost three times to transfer my purchases then it told me I just authorized three out of the five computers when we only have two in our house!  

It didn't sync my purchases from the backup either.  Another thing, the only thing that it synced was the voice memos from my recordings.  -_- 

If you guys have any alternatives or if I'm just out of luck.  Because the CDs have miraculously disappeared.  Things do that in my room.  Like my package of bookmarks.  Or my double disk of Grease 1&amp;2. Anyway.  It'd be great if you could help me.
This can definitely be done, one of two ways.

Free way and non-free way

FREE WAY


Download MediaMonkey, free version
Install and in preferences or settings modify (if needed) where you want things to be sync'd (from phone to pc).
Plug your phone in, sync.  It's not made by Apple so it'll pull every song off your phone and onto your harddrive
May need to move songs from the MediaMonkey location to iTunes location
May need to deal with some dupes


NON-FREE WAY


Read this article how-to-copy-music-from-your-iphone-ipad-or-ipod-touch-to-your-computer-for-free
Buy referenced software and follow their instrux.  Likely very similar to above steps


If you're going the buy route, check out this company as they make good stuff Macroplant iExplorer

Finally if you're on a Mac you'll need to substitute Doubletwist for MediaMonkey