I personally hate Configurator, it’s not designed well and it’s a very important tool in my life so here goes a What Not To Do, first.
The Apple Configurator tool robbed my school of @ 60×4 apps.
Here’s my mistake. I bought all the apps needed for the whole school in one lump sum. i.e. 350 copies of Pages. Then happily went to Configurator and loaded the spreadsheet. Installed on all the student iPads. Then need the remaining licenses to gift to the teachers and @ 30 for the cart. NOPE! Once they are loaded in to Configurator you can never get them back. Apple said, “sorry”.
I did this for the iWorks suite, iPhoto, & neu.Annotate before I realized what was happening.
This is what to do, in short. From the VPP account, buy the number needed for exactly what you need, just make sure, it’s over 20, even if you only need 11, 20 copies is cheaper than 11 because they are half off at 20 or more. Get the spreadsheet generated by the VPP site for the 20 then buy for the next cart or site, it will generate a new spreadsheet of 20 you can give to the computer and its copy of Configurator.
More on Configurator to come… UPDATE: To see how I really use it now check this post.