Well, I have used every MS OS except Vista, Slackware, Red Hat, and Ubuntu, not in any particular order.
By far my favorite OS is Ubuntu 6.06 (Dapper Drake). It works for me, I am comfortable in it, it works out of the box for most things, the rest I could get going pretty easily. All of the Microsoft OSes I've used worked better out of the box than Dapper, thats true. The problem is that it is for one reason only - drivers. If companies would make even a half-hearted attempt to support things in Linux it would be a million times better than it is now. (I still cannot believe that Lexmark does nothing with Linux at all, especially since it makes the Dell printers and Dells now ship with Ubuntu. I'd be pissed if I bought a laptop from Dell with Ubuntu and a Dell printer and they could not possibly work together.
I really liked Win2000 back in the day and XP pro got the job done for a while. That said, once I got comfortable in Linux and took a little bit of time to learn it, I love it much more than any MS product I have ever used. I know the argument is cliche, but I find it a lot more stable, flexible, useful, productive and comfortable than I ever did Windows. Switching to Linux can be like learning to use computers in general all over again.
I have never been able to do something under Windows that I could not under Linux. It might take some more time to figure out, but thats because you are using a new OS, fundamentally different.
For me, and OS shouldn't require "new equipment" or a powerful cmoputer to run, even XPs reqs were too much. An OS should be able to utilize those resources if available, and eye candy and extra features are great, I love them. But I can install Ubuntu on a brand new system and make use of all of its capabilities or I can install it on a ten year old system and it will run just fine, even be snappy to some extent and certanly usable if I use a little bit of sense when installing.
All that said, thinking back on my computing (pretty extensive) over the past 10-12 years I can definitely say that I like Linux a lot better and will probably never go back to a Microsoft product. I'm not going to say that MS is shit, etc; though you could make that case. But Linux can be shit for someone who does not know how to use it.
But, if you take the time to install a good distro and learn how to use it, the rewards will be great, and you will have a much more customizable, stable, fast computing experience.
Once again, just my thoughts and experience.