I've always recommended starting with Mandrake (now called Mandriva (http://www1.mandrivalinux.com/en-us/)). I think it's one of the easiest distrobutions to use. Personally, I use debian (http://debian.org), but that's for people who don't want a lot of hand holding. :)
As for windows emulation(implentation), I have no experience there, but you should take a look at wine (http://winehq.org/) also.