Zak,
The short answer is yes, it will work. I prefer Parallels over VMware. Note that you will need a minimum of 8 Gb of RAM on your iMac but I recommend 16 so that you can share 8 Gb of RAM with each OS. if you don't have 16 Gb of RAM, we recommend using Bootcamp. On the upside, you will literally be turning your Mac computer into a Windows-based PC with all of the available RAM but on the downside, you will not be able to click from the Mac OS to the Windows OS without rebooting. I recommend contacting your nearest Mac store to have Windows and your virtual environment installed.