First off, I love how ClassicPress is moving WordPress away from its attitude of casual corporate spirit and toward a business-oriented CMS. My question: Is there any practical, operational difference between migrating a WP site versus a fresh install of CP?
Welcome to the community, @edsuth. 
To clarify, ClassicPress isn’t moving WordPress away from anything. These are 2 distinct projects, both of which have their own goals.
It doesn’t make much difference whether you migrate or do a fresh install. With a fresh install, you’re getting all the files you need in the package. With a migration, the needed files will simply overwrite the WordPress files where needed.
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Thanks the the clarification, particularly the explanation that CP and WP are two distinct projects.
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Note about migration versus fresh install:
If you migrate, your installation will still contain a few JS files that are part of WP but not part of a fresh CP install.
If you then install Shield security plugin, it will realise it’s on ClassicPress and will flag those files up as rogue. But it does then give you the option to delete them, so no big deal.
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