This talk will touch on strategies and challenges we have encountered along our journey of hosting over 1,000 Django/Wagtail sites. Told in the storybook style of "One Thousand and One Nights" (a.k.a. "Arabian Nights") this talk will feature real-world anecdotes about: technical architecture, business challenges, financial challenges, customer support, and security challenges such as dealing with onslaughts of spammers and attack vectors.