Yup. It's a very good plan. The key is Accelerated C++. Just lock yourself in a room with a computer and a coffee machine and get through that book. It's short, well written, and contains examples throughout that you should be typing in as you progress through the book.
For pretty much everywhere the MS --> Mac move is considered, isn't the big sticking point Exchange Server?
AFAICT, everything else has a good replacement. It's the email server that has everyone locked-in, right? I'm not a Mac user though, ... maybe OS X can talk to exchange?