Do I need to partition storage space for windows 7 software?

I'm still debating if I should sell my Alienware and buy a MB Pro Ret and my main questions is concerning storage space.
I know that MBP can't compare to an Alienware gaming system but I hardly have time for that stuff anymore. I might play Skyrim every now and then, but that is the only game I care for really. I mainly want to have a light weight reliable laptop.
So... because I have so much software for my windows system now, I was looking into transferring that to the MBP. Lightroom 4, AutoCAD, Word and Exel, Photoshop... ext. ext. Which brings me to question:
Can I partition 50GB for the OS only and install all the software I have on that drive even if it wont fit on the Windows 7 partition?
In other words
Do I have to calculate how much space all my programs will take up for Windows 7 and partition that amount or do I only need enough space for the OS?
I have never owned a Mac and am not familiar with the OS, I was debating if I should partition 500Gigs and slowly transition from Windows to iOS and maybe one day get rid of the Windows partition and just have the iOS on there.
I don't know... that's why I am here... Apple has a great community so let the advising commence... haha.
Thanks for the help.
Dallo
Forgot to mention: If I do get a MBPR it will be the 2.6GHz, 16GB Ram and 512GB Flash

It's recommended to create the partition with enough space for your programs, but if you create a very small partition, install Paragon Camptune X or WinClone to resize the Windows partition

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