Well, Ubuntu is the free version of Linux. I'm currently using it to type this message. As far as functionality goes in the Plug n, Play field, Ubuntu seems to fare well. A girl at my college needed to charge her iPhone, she plugged it in my available USB port and immediately Ubuntu connects to it. Just for the fun of it I looked at some of her pictures to see if it would allow me to access them. Sure enough, unprecedented access to the files on that iPhone.
If you don't want to remove Windows, you can always repartition your current drive to make room for another Operating System. That's precisely what I did and now I have a choice between Windows Vista, XP, and Ubuntu. You can also use Windows with Ubuntu by installing it into a virtual machine using programs such as Sun VirtualBox. Then when you start Ubuntu you simply launch the virtual machine allowing you to run Linux and Windows on the same computer at the same time. Ubuntu also comes with Pidgin, and Internet messenger which can connect to most popular instant messaging services using your registered account credentials.
Ubuntu will give you some decent functionality when it comes to Linux. However, it still comes at a cost. As you already stated, not all your desired applications will run with Linux. So you will either have to try the virtual machine method or just suck it up and drive on.