you have to figure out how much data you want/have to transfer. If it's several hundreds of GB, it will take a while, and you should use the fastest available connection (firewire to firewire maybe? Of course an external thunderbolt would be perfect, but who has that)
transfering data works just fine and simple. It takes as long as it takes to copy the stuff physically.
transfering apps basically means installing them, because no Windows app just runs on OSX. It is not any more and not really any less work than on Windows. Installing on OSX usually requires less "next" clicking but otherwise you still have to download installer packages. You still have to let the install routine run its work or let it unpack the packages.
It is less clicking but takes about as much time as on OSX unless it takes you very long to find OSX versions of your apps or getting hold of the installer packages.
I don't recommend Office for Mac (2008, 2011). It sucks I still write my papers and stuff in a VM on Office 2010, because the Mac versions lack features, have a bad gui, and are really slow.
For small stuff that isn't worth launching a Windows VM just install Open Office or LibreOffice. Office for Mac is a waste of money and if you already got a Office 2007 or 2010 license keep it and use it in a VM in Unity mode. Trust me that works much better.