I created a custom field group, called "Gallery" and I assigned it to Page post type.
I added a repeating filed, called "Gallery Element" with two fields: a plain text one called "Title" and a picture one called "Picture". Both fields are required.
When I add Gallery Elements to the group and I select the picture through the media picker, only the first Gallery Element -> Picture field is updated, even if I am trying to add or edit the Picture field on a different Gallery Element.
If I save the post, and thus the page reloads, I can add a new repeating field, if I add a second one, then it shows the bug.
I managed to reproduce the issue on 3 sites, two of them using Type 3.2.7 and one using 3.2.5.
I just got the news that the fix will be shipped with next release of Types version 3.3 that is scheduled to set to release in a couple of weeks from now.
I'll keep you posted once we published Types 3.3 officially.