Why not make map series available to each map on a layout, not to the layout since, for printing purpose, you can have many map sections of a series of one layout? Since annotation is a link to a map series is very awkward to offer the annotations displays and show specifically for each page but only for one map per layout.
For me that is for map 1 and 2 on a layout, you have a clean map 1 and the map 2 with double text since the series does not take on the display. We have to return before datadraven now map series, and make the best fit between two maps.
I know you can duplicate maps to point to different extents. (How To: Set up a page layout with multiple map frames that reference the same data )
By the way, since Pro projects use a lot of memory, duplicate maps are not the best way to manage projects.
A good improvement, in pro, will be to allow a layout with many map view pointing to the same dataset to have a different extend for each view link or not to a map series.