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Best plug and play Linux

I would say probably Ubuntu or Linux Mint IMHO,Zorin is user friendly as well.

As to Windows to Linux it depends on the app in question.
 
Straight Ubuntu is horrible for first time users IMO. Try Mint 17 or Zorin like Mem suggested. Those are noob distros designed to get users accustomed to a Linux based system.

Porting windows apps to linux isn't an easy task. Wine is available but I recommend hitting up the software manager and trying to find similar software. Chances are what's available on windows has a similar counterpart available on linux.
 
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