Transition from Windows to Ubuntu
Since I have almost no experience with Linux, I chose to install Ubuntu on a separate hard drive, and dual-boot with Windows until I get everything figured out. I'm not sure if this is the best idea, since I'll still have a crutch to fall back on. If I were "upgrading" to Vista, there would be no turning back, so I'm not sure why I'm being so cautious here, but it seems like the safe thing to do.
The installation went surprisingly smooth! Compared to installing Windows, it was a breeze! This is certainly encouraging. All the normal stuff was installed by default, the updates ran automatically, and didn't even have to reboot 42 times. Having OpenOffice and Evolution is comparable to MSOffice and Outlook, and I didn't even have to install anything extra.
There are a bunch of optional packages that are easily installed from the "Add/Remove..." application, and they're all free.
So far, I'm not seeing any fatal flaws or show stoppers in my plan to switch completely to Linux. I'll get it all figured out on my PC, and then I'll go ahead and roll it out to the rest of the family. The goal is to be completely switched over by the fall.
One significant thing to note here is that I'm not switching because it's free, I'm switching because it's better. We're relatively happy with WindowsXP, but we're going to have to switch to another operating system in the future, and it looks like Ubuntu is the best choice.