XP to Win 7
notes: he will be upgraded to Windows 7 Pro, we are a K-12 Education Environment with a mix of PCs and Apples
You can download a trial copy of FileMaker 11 to his current machine and try converting it to see what you get. Some conversions will run very smoothly, others will require more "adjustments" to the orignal design before they work in FileMaker 11.
Here's a knowledge base article you may find helpful: http://help.filemaker.com/app/answers/detail/a_id/750/kw/converting