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Long-term Free Software Transition
If you're nervous about switching to free software, I totally understand. There's a method that colleagues of mine have used to great success when moving an associate or relative to GNU/Linux.
In short, the way it's done is to change the programs you use one at a time to free software equivalents. Then, once you're using free software for your workflow, switching operating systems will just be one more program to switch, and it shouldn't disrupt your way of life in the way that going from almost 100% nonfree software to mostly free software (there are inevitabilities) could.
If you're interested in this kind of transition rather than a quick switch, send me an e-mail, and I'll see what we can work out.