I don't know about your first question.
As for having a CI server automatically update the packages, it's doable in theory. You could chain the "List-Package -Installed" and the "Update-Package" commands and have each package updated to the latest version. See the command reference for further details.
Scott Guthrie says this on the topic:
  "You can integrate the command-line
  option with a CI solution and do an
  update-package command explicitly as
  part of your build/CI process to pull
  down updates.  Frankly I'm not sure
  that makes sense for the scenarios we
  are talking about, though, as
  typically you want some dev to decide
  before updating a core runtime
  dependency to a new version.  NuPack's
  default model would have a developer
  use NuPack to install a library - and
  NuPack would automatically check in
  the package and dependencies to source
  control.  That way another dev (or the
  CI server) wouldn't need to use NuPack
  again - they could just sync their
  source and build.  But as I mentioned
  earlier - if you wanted to explicitly
  do an update as part of your CI
  process you could."
Edit:
After your comment I see what you're trying to achieve. I found this long thread in the NuPack discussions list about the issue. A solution will apparently not be part of v1. A custom build task in the CI of your choice and a config in your repo for it is the only solution I see. Please report back with your findings. You got me interested.