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I'm in webdevelopment many years now and switching from php to ruby was a step I'll never regret. About the sysadmin perspective, I manage all my servers myself, used debian on my workdesk long enough to do this, and in the last year with all the stuff like bundler and the new rubygems.org it got so much easier. If you need it even more easier then Heroku is something you won't get elsewhere.

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