multistep.py

from operator import or_
from functools import reduce

import inquirer

types = {'web': {'directory brute force', 'httrack', 'drupal scans', 'web app'},
         'ssl': {'ssl audit', 'web app', 'drupal scans'},
         'infra': {'nmap common', 'nmap all tcp', 'udp', 'windows audit'}}

def assessments(answers):
    choices = answers['types']
    return sorted(reduce(or_, (types[c] for c in choices)))

questions = [inquirer.Checkbox('types',
                               message='Choose assessment type(s)',
                               choices=sorted(types),
                               validate=lambda _, choice: bool(choice)),
             inquirer.Checkbox('assessments',
                               message='Choose assessment(s)',
                               choices=assessments)
]

choices = inquirer.prompt(questions)
if 'web app' in choices['assessments']:
    extra_questions = [inquirer.Confirm('parallel', message='Should the web app test be run in parallel?', default=True),
                       inquirer.Confirm('http-only', message='Should the tests skip TLS endpoints?')]
    choices.update(inquirer.prompt(extra_questions))

print(choices)