jetsci's Journal: Internal Government Software

I work for a rather large branch of the Canadian Government(read, Communication Regulations). We use a great deal of custom apps for the purpose of tracking licensees and such. None of these apps are particularly demanding - simple database front-ends. However, we're required to run Win2k and will soon be 'Upgrading' to Vista. I'm rather apprehensive about the whole move. Windows 2k is serving me well at work but I miss my Debian desktop machine and am considering booting from a live CD. My concern is making my apps run with wine and not being detected internally as an unauthorized system(we use software to confirm OS machines associated hardware to gain access to network - among other things). Can I pull it off and maybe convert a few colleagues in the process?