Looking for a way to bulk assign by task set in the same timeline

We have task sets for different products/services but many of them include the same role. There are instances where the resourcing manager would like to assign one set of tasks to one person on the team and the other to a different person on the team (both with the same role). Currently, the resourcing manager is bulk assigning all of the tasks to the one team member and then has to manually change over the task assignments (line by line) to the other team member with the same role. We've tried using filtering when bulk assigning to assign one task set at a time but we're running into issues. Has this come up for anyone else? If so, do you have a solution?