As has been said, the best idea is probably give Ubuntu a try via the Live CD route. Its come a long way over the years and is easy to use. I've put my dad on it (it was a challenge to get him to use the mouse) and he's very happy with it.
Like everything else, it takes time to get used to new things. It's not Windows, so you'll need to get used to where everthing is. However, you shouldn't really need to go anywhere near crytic configs unless you fancy venturing under the hood. The menus have all the options for changing settings. I'm currently running it on my laptop (I'm a software dev by the way) and have been for a number of years.
I'll tell you one thing - out of the box ubuntu beats any windows version hands down in driver support. Only recently were there issue on laptops with wireless drivers. That seems to be pretty much solved these days.
Your only issue as has been mentioned is gaming, but that can be overcomed with a dual boot system. I'd advise you to read up on some tutorials and see if you feel comfortable with doing it. It's not really that hard at all.
Otherwise, there is plenty of free software that works just as well as the paid for M$ version (open office for a start).