Reporting on Users in a Subgroup

Hello. I am attempting to run a report on users in sub-groups. Is it possible to group a report by Sub-group, and within that group show each user’s last login date? Also, is it possible to group by users who have logged in the last month, while having another grouping showing everyone else?

The end result should be a report that shows all users, grouped by sub-group with their last login date displayed. Has anyone accomplished something similar to this? Any help would be greatly appreciated!