Make a custom column sortable by a value from a different custom post type

(I was going to add this as a comment as it’s not a full answer, but I can’t yet…)

I think you will need to use an SQL query as the standard meta_queries / orderby won’t work. Have a look at Custom Table Column Sortable by Taxonomy Query and http://wpdreamer.com/2014/04/how-to-make-your-wordpress-admin-columns-sortable/#sorting-posts-option-b for a couple of examples.

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