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I've always thought 10 was the magic cut-off. I can imagine running "apt-get update && apt-get upgrade" ten times in a row before I get annoyed. Any more than that and I'd want scripting.

Really there's nothing stopping you from automating "some" machines and later pushing that out to the rest of your hosts. (Or just setting up trivial automation "configure NTP", "Disable root logins", "Append 'steve' to sudoers" - and keeping doing the rest by hand until you're confident.)

FWIW I use my toy configuration system, slaughter:

http://www.steve.org.uk/Software/slaughter/



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