That the management is on your side is a big plus. However, it is hard to change people's habits. I think the final step that motivates you to learn something new for a lot of people is when the old way to do it becomes too cumbersome. I started using CVS when it was just too much effort to back up different versions, find out when I made a certain change etc. :). So breaking the old system is not too bad an idea...

I'd try to talk to management about this. Develop a plan together to introduce a better system. If your company is a professional development shop, I am sure they have coding guidelines, prescribed programming environment guidelines etc. It is hard to change a project that has already going on for a while. Why not choose a new project, maybe even with a couple developers that are still rather new to the company, and try to implement some of your changes there?