A complecated schedule generator :confused::confused::confused:

I am trying to figure out how to make a schedule generator for a Surgery Class rotation. There are a certain number of jobs needed each day but during the rotations each person must at minimum do each job twice with the exception of 2 of the jobs. There are 22 positions each day at minimum. Need a chart to randomly generate the order of jobs so that the job position quota each day is met (the column) and the number of min/max times that job is done by each person is met over a 12 day rotation period (the rows)

So with that information in hand How do i go about doing this exactly? because once this is created i want to write a program that will do this at the click of a button after inputting the number of students. In that manner it will randomly generate a base schedule with some blanks to be filled in manually taking out about 90% of the work and minimizing the time consumption it takes to write these schedules.