user_combinations.py

#!/usr/bin/env python

from itertools import combinations

USER_TYPES = [
  'Instructor',
  'Course Preparer',
  'Mentor',
  'Student',
  'Observer',
  'Administrator'
]

user_combinations = []

for n in range(1, len(USER_TYPES) + 1):
    user_combinations.extend(list(combinations(USER_TYPES, n)))

with open('output.txt', 'w') as f:
    for line in user_combinations:
        f.write(' '.join(line))
        f.write('\n')