Right now I mainly use Debian. I've messed around with Ubuntu, and I put it on my little brother's box, but I don't like it myself. Too many choices are made for you, in my opinion. Its definitely a good starter distro, especially for someone coming from Windows. I'll probably will end up running it on one of my other systems, because it does have some nice features. I'm also going to try out Fedora, but I've been holding out on that until Fedora 11 comes out, which I think is in a couple days.
As far as Wine goes, I've had no complaints myself. A couple games I've tried haven't worked, but they're years old and were never popular. Everything else I've tried works well.
After using Linux though, I'm beginning to see how ludicrous it is to pay hundreds and hundreds of dollars for an operating system. It just doesn't make sense, personally. Besides that, its just annoying that Windows and Mac don't have the multiple workspaces like Linux does.
What about desktop environments? What do you like to use? Personally I like Xfce over Gnome or KDE, but I've been thinking about trying out some others soon.