Q: Syncing up iTunes to my devices . . .

Try reinstalling the latest version of iTunes on your computer from here -> Apple - iTunes - Download iTunes Now

If that doesn't do it, try what is described in this Apple doc -> iOS: 'Not enough free space' alert when trying to sync

== Error -54 ==
From an OS9 reference, error -54 is a software lock on a file or a permissions error. (Some of the old codes still apply to OSX although there is no formal list of OSX error codes.)

First, try simply restarting your computer.

Try quitting iTunes, then deleting the .xml (not .itl !) version of the library file in the iTunes folder (iTunes will generate a new one).

iTunes Library cannot be saved (Error -54) - https://discussions.apple.com/thread/1912814 - various things to try.

Unknown error (-54) while syncing ipod - https://discussions.apple.com/thread/1082953 - problem was locked files

Why does iTunes keep showing a -54 error when I sync my iPad? - https://discussions.apple.com/thread/3727114

Error -54 possibly related to Touch Copy - https://discussions.apple.com/thread/3727114 - cleared by deleting preferences on iPad.

iTunes: Missing folder or incorrect permissions may prevent authorization - http://support.apple.com/kb/ts1277

Troubleshooting permissions issues in Mac OS X - http://support.apple.com/kb/HT2963