AndrewHickey comments on I want to learn programming - Less Wrong
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I take your point, but disagree. Cygwin isn't especially user-friendly, and modern GNU/Linux distros are trivially easy to install as dual-boot systems, so there's no real commitment there. And if you're using a real GNU/Linux distro then you'll be able to find help for your exact version of the software much more easily - cygwin has a fairly small install base by contrast.