I started using Ubuntu Linux about 3 years ago and currently going on to my 4th year using the operating system. There were some hiccups at first when switching over, but now looking back, I have found the process to been a worth while one.
The greatest benefits to me about using a Linux system is the ease of reinstalling software and getting original settings back after a fresh install. I still remember times when working on a Windows computer where I would reinstall the OS once or twice a year to freshen things up and spend 2~3 days getting the system back up again with all the software that I use and configuring everything to my liking. What a pain that was.
The difference with working on Linux and having a home directory where all one's settings are stored in (somewhat) hidden folders, is that as soon as program is reinstalled, the home folder is the first place the program looks for to get the setting information. So long as you backed up the home directory, the instant you reinstall software, it is automatically configured. The other great thing is that software can be batch installed from repositories, and instead of having to deal with installation dialogues, you just tell the computer to install the software and it automatically installs them to a binaries folder and things are automatically setup. If you have multiple users, everyone's home directory holds each user's personal settings so there is no clashing whatsoever. Everything is simple to install and fast to restore.
The other great thing is having free software and having a repository to download whatever you need from. Just download the software, give it a try and if it works great then keep it. If not then uninstall it and try something else and most free software out there is "good enough" for all practical purposes.
There have been times that using free software didn't work out for me because of some minor formatting or incompatibility issues. For example, while open office can open and read MS Office files, there are times when the formatting of documents get a little off. I had the unfortunate problem of trying to write and update resumes in open office to find that the alignment of text was just off enough to make the document look a little unprofessional. As a result of that, I've become a little bit of a fan of PDFs, once you convert the document into a PDF, it should display the same across all systems.
If worse comes to worse, with the advent of OS virtualization, I am now able to run Windows inside of Linux or Linux inside Windows or what have you. I think this is a great boon to trying out new OSes and also getting access to just that one application that you can't find on your native OS. Rebooting is such a pain as I generally don't like needing to close all my applications and then open them all again after restarting the computer. Right now I use Win XP in side of Ubuntu just for MS Office on the rare occasions to edit documents, but other then that I don't use Windows for much else while at home.
To be honest, I don't see any real argument for the need to be dependent on a single operating system anymore. Most of the best software are multi-platform now and using them is just a matter of installing them onto whatever OS that you're on. Even writing multi-platform applications is not terribly hard using languages like Java or even Python since just-in-time compiling is sufficient to create native code for the applications to run.
So there really is no real need to be totally dependent on a single operating system anymore for any reason other than for the comfort of a familiar interface. To be honest, I think that Microsoft is walking on hollow ground; the instant the ground gives, I think it will be all over for them.
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