I love Puppet and make my living off of it, but I'm not so sure it's a great suggestion here. The OP should be using PXE to boot into the installer, automated by the standard OS automation framework, Debian Preseed. Puppet can be installed in the late_command, if you really want it. I would argue that if the OP is asking this question in the first place, Puppet may present too steep a learning curve and too much work. An SSH pubkey with capistrano should probably be fine for modifying things later. He is only setting this up for an 'event' so ongoing config management such as Puppet is probably not necessary, too complex. If OP wants to set everything up first then copy that box, you can use debconf-get-selections --installer i think is the command line to get only installer values.

That shit about the mayor is rich! I'm not sure I even believe the Bostonian bit at all. I grew up north of Boston and live in Boston- so unless he moved to New York or another city with a "Little Italy", he is lying. We call the Italian ethnic enclave part of town the "North End". Only a tourist would call it something like "Boston's Little Italy".