I have been using Ubuntu since 2007 and Wine has helped me run quite a few of my old Windows games (SimCity 4 among them. I do not know the current state of Wine, but I never had trouble running SC4 a few years ago). But if you want to play Windows games, your best bet is to forget Wine and have Windows either on another partition or on another hard drive. Nowadays, Linux is still my main platform for everything from browsing the internet to attempting to learn game programming (I always get bored and give up) to writing a book (I always get writer's block and give up), but when I want to play Windows games, I will boot Windows 8.
And yes, Steam is a great choice if you cannot have Windows right now. You can play Euro Truck Simulator 2, Mount & Blade: Warband and Crusader Kings II on Linux, which should be enough to keep one busy for months.
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DISCLAIMER: It should be noted that, while I strongly suspect I have Asperger's syndrome, I am not diagnosed. Nevertheless, my score on RAADS-R is 186, which makes me a pretty RAAD guy.
Sorry for this terrible joke, by the way.