One possible approach to these issues is to combine Chromebooks with third party solutions such as Ericom AccessNow, an HTML5 RDP solution that enables Chromebook users to connect to any RDP host, including Terminal Server and VDI virtual desktops, and run Windows applications or desktops in a browser tab.
FORBES: Google In Education: Chromebooks A 'Right Time Technology' For Passaic, New Jersey School District