Hi there, Noah!
You will not be able to get a better picture in front of
Cinderella Castle than you can at the very end of the night. The deserted park combined with the magical glow of the lights really makes for an amazing picture. If you happen to catch the twinkling Kiss Goodnight, you are in for an extra special treat.
Noah, I am so happy to tell you that the Kiss Goodnight is happening mostly every night. The exception to this would be when an extra after-hours event, like
Disney Very Merriest After Hours, is scheduled. The Kiss Goodnight generally happens about 30 minutes after the park closes, so take your time exiting the park, and perhaps do a little shopping along the way.
The added benefit to catching the Kiss Goodnight is that the crowds will be a whole lot lower when you are exiting the park than if you were to depart right after
Disney Enchantment.
Wishing you sweet dreams, Noah!
Sarah B.