Bit of background - I have had 7 years in IT, and three years of that I was a full time Apple Tech specialising in Apple Laptops and OS X (note this is in the past. I no longer work directly in IT support...thank god). I currently have a Macbook as my main laptop (three years old) and two Windows 7 machines. Personally, I love the Apple UI. It's great for web browsing, chatting, all the basic "normal" things that most people do on a computer. It's robust, well built, and pretty. It's also incredibly expensive comparatively. Sure, there are Sony Vaio's etc that are similarly priced, and there are $399 laptops, and everything in between. The reason I went mac when I had this laptop was because I wanted a small form factor with a 13" screen. At the time, you would pay a HUGE premium for that in all windows based PC's. These days, you can get 13", 15", 17" with no real premium (I'm looking. The choice is incredible, and I can't see any reason why you'd pay, in a lot of cases, around double the price for an Apple based computer, unless you KNEW it was going to make your life easier. Personally, if I had to replace this machine, I'd get a Lenovo E320/420/520 or similar for around half the price of the Apple equivalent. In terms of your concerns such as accessing all old stuff, you're no worse off with a mac than you would be with a Windows machine, but your concerns of certain sharemarket software not working might mean the cost of a virtual machine program and a windows licence anyway.