There is a good series of 'Missing Manuals', one of which is a great book for transferring from PC to Mac. You can do almost everything on a Mac that you can on a PC (and more). There are easy ways to transfer (eg contacts etc) from outlook using pragrams like O2M from little machines and the 'missing sync' which allows you to sync from mac to win compatible phone.
However its just as easy to run windows on a modern mac. Leopard comes with a facility to boot into windows. You can also use virtual machine software like parallels which allows windows to run at the same time as the mac OS. (You will have to obtain a copy of windows). So you could continue to use your current windows based music and sync routines or switch totally to mac. If you already use itunes it should be much the same on the mac.
Missing Manuals
Little Machines