Can AI tools craft a New York survival guide for the city's most unique and peculiar challenges? From maneuvering groceries in fragile paper bags to unexpected AC water drips, can these machines generate speculative solutions? The AI tools employed in this guide are ChatGPT (Version 3.5) and Midjourney (Version 5.0). ChatGPT initiates prompts and ideations, subsequently transferring them to Midjourney for idea generation and imagination. All solutions and images remain unedited.