Thank you all so much for the feedback! Some really great points here, I've decided to remove the dragon from the top sample for now.
An email, as well as a letter with pictures of both examples have been sent to Glenn Hendricks (Mayor) and Gustav Larsson (Vice Mayor) of Sunnyvale, CA. I'm dedicated to making this happen, but I understand it'll be a process. I wanted to stop by and share this with you all. Feel free to voice your opinions. I'll be sure to keep in touch as this project develops. –Evan