In 2 to 4 weeks you’ll have a smile plastered from ear to ear
Unless you start on Gentoo, as someone else suggested. Then in 2 to 4
weeks you may manage to get it to the point where printer and sound
card work. I’m not bashing Gentoo, but it’s a distro for hardcore
Linux tinkerers. Suggesting it as a first distro to a newbie is a sure
way to scare people away from Linux.
Ubuntu is a good choice because it is probably the nearest thing to a
“decent desktop OS that my mom could install and use” in the Linux
world today. Why is that a good thing? Because, as a Rails developer
you want to spend time on productive pursuits, rather than trying to
figure out how to make your VPN connection or MP3 player work.
As far as Rails development is concerned, I saw next to no difference
between Ubuntu and Debian. Except that you have to install more
packages on Debian to make it all click together. Please enlighten me
if there actually is any.
There is no point in building your own Ruby. You can safely use what
Ubuntu provides. Building your own Ruby well (i.e., with support of
zlib, openssl, readline etc) is not too hard, but actually is not easy
for a Linux noob.
Ruby development in Windows is not such a big pain, either. Sure,
command-line experience sucks and your unit tests take longer to run,
but none of it is really unbearable. As long as you use One-Click
Installer Ruby, and not Cygwin’s.