iPhone files not showing up on Finder
Ok I figured out whats wrong. See this thread for an answer (TLDR: iTunes database was corrupted) https://discussions.apple.com/thread/4474508


  DO NOT RESTORE
  
  It could be one of two (or both) files are corrupt on your
  iPhone (or other iDevice), they are
  iTunesDB andiTunesCDB.There
  is an fast fix for this, even if your
  iDevice is non
  jailbroken.You want to disconnect your
  iDevice from your computer and close
  iTunes to ensure you DO NOT
  RESTORE.Download iFunBox or
  iTools a Free Tool for accessing the
  iDevice file system. It has both a OSX
  version and Windows version for
  download.After you download the version of
  iFunBox or iTools for your OS, you
  will need to install it and run it.After installing and
  running iFunBox or iTools, connect
  your iDevice to your computer.You will see a
  message in the Upper Right of iFunBox ”connecting to
  iDevice“, after iFunbox has
  connected to your iDevice, click on the tab
  “iFunbox Classic“.On the left panel, expand
  “Raw File System” (click on the +),
  then expand “iTunes_Control“, then click on
  “iTunes“.In the right panel you will see a
  number of files, right-click on the file
  “iTunesCDB” and select rename, please add X after the
  iTunesCDB in the file name, this will allow you keep
  the file in case you need it again (you should never need it, but
  better to be careful than sorry.) Do the same for iTunesCDB, iTunesControl and iTunesPrefs. After you have renamed the file, click on your iDevice name on the upper right
  of iFunBox and select “Device Safe
  Removal“, this will ensure the file name change will be
  written back to your iDevice.After you see
  your iDevice is closed (“No device connected” will be
  displayed in the upper right), you should now close
  iFunBox
  
  Now run Apple iTunes, it will see your
  iDevice and you will be able to Sync again.