Whether in ArcGIS Pro, ArcMap, or in the browser, my suggestion is simple. Due to the obliquity of many types of aerial imagery, I suggest that there be a function that lets users open up the raster layer in an electronic light table (ELT) and exploit from there. I have seen "image space" but what would be more useful, much like the FMV viewer, is an ELT that opens in a separate viewer, honors the obliquity of the image, and where the metadata of the imagery intersects with the maps metadata, the annotations as features reflect on the map view. Additionally, within the ELT options, users should be able to select which feature class and geodatabase they are connecting to updating and editing. ArcGIS Pro allows simultaneous 2D and 3D views; why not an Image View as well.
A web ELT would integrate nicely with ArcGIS Enterprise. I would personally like to see the WebELT be a widget in the same tab, but I understand that it could limit the functionality and experience into a smaller view. If in a separate tab, there should be an option as to which portal layer users pull in and update/edit.