A friend of mine is a total fan of the Sun Unix Workstations. I worked on some Sun Ray Terminals at our local university, and, well, one could feel how old the Solaris was. KDE 3 or MWM were the Window Manager choices. My work partner was rather stunned when I switched to MWM, and used vi for coding.
Dual-Boot systems are always a great way to get used to Linux. I've started using a dual-boot system, and then I suddenly realised that I haven't booted Windows for a year. And now, on my current notebook, there is no Windows anymore. On my Desktop machine though I keep a running Win 7 for gaming purposes.
Most simple Windows software can be used on Linux using the Wine project (acronym for Wine Is Not an Emulator), which reimplements the Windows API. DirectX is tricky, but office applications usually work. And seriously, you'll be surprised how much of your software can be replaced by Open Source. Currently I use LibreOffice as Office Suite, Gimp as photo editing software, DigiKam as photo management system, and many more. I even looked into FreeCAD, and was surprised how well it can be used.
And Masterpiece:
It depends on the Desktop Manager you use. Some don't even have a taskbar from the beginning on. In most Desktop Managers though you can run software directly by pressing ALT+F2, and then entering the name.