Here's a school that actually did transition to Linux: http://searchopensource.techtarget.com/originalContent/0,289142,sid39_gci1245710,00.html They didn't use Wine. Here's what they said about legacy windows apps:
"Using Wyse terminals, the district also planned to offer students and staff thin-client desktops running OpenOffice.org. Ericom software – a Citrix alternative -- enabled the terminals to run the district's existing and irreplaceable Microsoft Windows educational applications, including Type to Learn, Reading Counts and Kid Pix." - Dan
