makeowlist.py

#!/usr/bin/env python3

joiners = ['', ' ', '.', '_', '-', '+', '!', ',', '~']
mains = ['main', 'Main', 'MAIN']
permutations = []

with open('owchars.txt', 'r') as f:
	lines = f.read().splitlines()
	for line in lines:
		for join in joiners:
			for main in mains:
				permutations.append(line + join + main)

[print(perm) for perm in permutations]