I’m a fan of the oak theme and history/colors, and I agree with @KenAA that the squirrel is a great idea for a city mascot. But I have to disagree on this being “simple enough to clearly see” as a flag.
From the City of Raleigh Flag - #5 by John thread:
It’s important to come up with a distinct look and symbol for a Raleigh-like flag. But do we need to sacrifice the utility and best-practices of a flag, in the process? With these principles in mind, I’m wondering if this design would still fall under the trope of “overly complicated and hard-to-see flying paintings made by those Americans and their towns”.