Either! Both are totally acceptable. If you want to look more realistic, then paint your face. For a scary clown like Pennywise, a mask could be better, depending on the quality of the mask.
You should do both. Washing your face first gets rid of the excess dirt and oil, making the mask more effective. Washing your face afterwards gets rid of any residue...
Once a week or so should be good. Don't do it too frequently. Oily skin can be treated with masks more frequently, about two to three times a week. Yogurt...