Best Practice for User Groups

Hi,
Is it possible to assign users to user groups both directly at the user level and simultaneously add multiple users from the user group level?

Both User and UserGroup are datatypes in my solution.

Yes it is possible

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Just by Workflows and List of users og User Groups and List of UserGroups on Users? You assign it to the user and to the User Group at the same time in the WF?

Yes. Whenever you want to update two data types at the same time you need a workflow action to make changes to the data type, one for each.