OK. I'll apologize for being a bit trite. Here is an intellectually honest core dump on Linux. Read it while listening to the Grateful Dead!
You can look at the Linux from two perspectives. One is as an end-user workstation and the other as a back office server such as a platform for a database server, file server, etc. The server side's pretty good; the workstation, not so much.
Frankly, if the "free" workstation stuff was really as good as Windows, no one would be paying for Windows. The freeness of Linux works to constrain it. So instead of one windowed interface benefiting from all the efforts put forth, the Linux teams are splintered into many incomplete competing interfaces, i.e. KDE, Gnome, X, Motif, CSE... Then of course there are many "flavors" of the whole thing, Ubuntu, Red Hat, Suse and many, many others. They all have their own GUI configurators. Some are open and some add proprietary stuff and they are all a little bit different. OpenOffice.org has never been on par with MS Office and there are many third party products available for Windows that are not available for Linux. I believe that Windows is still by far the best end user workstation going.
SERVERS ARE ANOTHER MATTER ALTOGETHER. Because the user interface is not really a factor, and because server configuration is usually pretty simple, the configuration challenges are muted. Linux as a database server platform, communications server, file server and web server is pretty darn stable. We run it here to host a z1090 mainframe (essentially a 390 virtual machine) and it runs for months on end without intervention.
Linux is often "device driver challenged". The common devices are there, e.g. Intel drivers, etc. The uncommon items, off-label printers, communications cards can be difficult and often Linux drivers lag the market so new devices often don't work with Linux. Some vendors are better than others at providing Linux drivers. Intel is good, ATI and NVidia do pretty well now and others. Stick with the popular hardware. You're safe with Intel chipsets on the motherboard. I have no experience with AMD although I am told they provide drivers.
A WORD ON GUI vs. FILE CONFIGURATION: If you go on the web and ask for help, your good-natured Google-mates will ask to see your configuration files and will offer their answers as suggested changes to your configuration files. You might as well learn to manage the files up front.
HERE IS A USEFUL FACT THAT ELUDED US FOR SOME TIME. "EVALUATION" VERSIONS OF LINUX DO NOT EXPIRE! If you sign on to the distribution sites like Red Hat or Suse, etc., they lead you to believe that you have to pay for access to their latest production builds. The offering of "evaluation" versions is designed to help you make an assumption that you have to pay to use them. But that, for the most part, is not so. The distributions are built under an open source license. As such the distributor can't charge for the software. Download the evaluation version of their latest build and use it. Ignore all the solicitations, warnings and the wailing and gnashing of teeth, etc. It will not expire. To do so would be a violation of the open source license they agreed to follow. They can cause components to expire if the components do not use open source code, even if they run on Linux, Oracle's database server for example.
The distribution companies can and do charge for what amounts to be "Windows Update" (Which you get for "free" with Windows, after you buy Windows) and they can charge for add-on software as long as the features in the add-ons are not extensions of open source code. If you decide to bet your business on your shiny new Linux server, buy the updates product with some support. It is my belief that, over time, the support will cost you more than a license for Windows Server. However you can clone the server as many times as you like without paying an additional license fee. That is pretty nice. Of course you will have to manually apply maintenance for the machines without a subscription.
There is loads of free information about Linux on the web. Try to focus on what you are trying to use Linux for. If you plan to administer a server, grab the latest evaluation version of Red Hat or Suse, set it up, back it up and play with it. Restore it if you fry it. VMware workstation is really useful for thin kind of learning. Google for help.
Try this link for Quality Advice it is probably the best bang for the buck in terms of getting quality advice. It is actively monitored for quality answers. (http://www.experts-exchange.com/)
Cheers, Tom