If you've never used a small screen with Linux, you may not know that you can click and drag a window around to navigate, even when you can't see the rest of the window on screen.
Some menus won't scale to the small size of the PiTFT, so in order to accommodate this (for example: wanting to copy over the contents of the USB stick to update the GIF folder on the Desktop) just use Alt + Left Click, while clicking on the body of the window, to drag it around so you can resposition it to click through the prompts.
Otherwise, you won't know what you're agreeing to when it asks if you want to overwrite, or skip.
A huge thanks to Ryan Sumner for providing the HTML that makes this slideshow happen. He went above and beyond a basic question, and provided an exact solution.
Also, a big thanks to Thorin Klosowski of Lifehacker for having the brilliant idea of using Kiosk mode in Chromium for animated GIF displays. Lifehacker article