Are there any best practices for doing this? More specifically: is it good to create a new instance and move the contents from the old instance successively or should I try to upgrade the old instance directly?
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In my experience, the first approach is often smoother: create a new instance and copy the database and assets folders (javascripts/, stylesheets/, images/). I also like to put all extensions that are available as gems in the Gemfile, instead of blindly copying vendor/extensions/. Also check the "old" project's config/environment.rb to see if the extension load order is defined or gems are included.

Benny Degezelle
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