yes, you can do that. However, you need to create two steps for this.
Each step can only hold one notification and one reassignment, but also a timeout. So, you would do a task "User-Task" assigned to the user, which reminds him after one day, and gets reassigned to GV_Supervisor another day later.
After a total of five days, the "User-Task" will time out - the "Timeout-Exit" leads to a step which assignes the workflow to "Admin", and then back to the "User-Task".
Greetings from Germany,
Simon H. Hellmann
DocuWare System Consultant