Much of what I know about this thing comes from either information in the papers I have read, or from one of the team members, named Jeanne, who I have contacted recently. So, take this all with a grain of salt, but I'll lay out as much as I can.
Starting in 2006, a team was put together to create a console, which aimed to be an upgrade to the DSi, with AI capabilities. They called it 'DSAI', originally code-naming the project 'Nitro-Intelligence'. The team had the leader Andy Fairwell (My father), head coder Silvia Graye, artist/coder Ava Lorde, writer/coder Jeanne Heathers, and graphic designer/coder Jack Davis. There were more, but these 5 are the ones most involved. Unfortunately, most of the team are dead, leaving Andy, and Jeanne as the only survivors today.
The first game planned for the handheld was New Super Mario Creator, a game which used a repurposed level editor, along with AI capabilities, but it wasn't until later on where the first concepts of the Princess Silver AI were worked on. The game, however was left extremely unfinished after several incidents left the DSAI cancelled. A high definition remake of the logo, along with other information about the game can be found below!
This is the course select screen. Barebones, but it works!
The level generation screen. Here, you were meant to play with the touch screen, and draw shapes, and the AI would interpret them into level geometry.
The maker screen, also pretty barebones. Here, you can press the Princess Silver icon to ask for her to help.
The VS race mode was a mode where you can race against Princess Silver in levels you made, or even ones she made.