I think that’s a surprisingly good idea for civic branding. We don’t have to present our city as something perfect and edgy; it can be a bit more realistic or self-deprecating in a humble way. I’m reminded of Greenville, SC, and how they’ve managed to create such a brand — “Yea, THAT Greenville.”
They’ve come from nowhere to be one of the most promising cities in the South, and I’m of the opinion that their tongue-in-cheek slogan has helped them. Like Raleigh, they didn’t have much of an identity, and essentially had to create something from scratch to draw people in. Unlike Raleigh, they had the unique challenge of having to stand out against over 30 other places in the country with the same name (including one in NC).
We’re not in the exact same situation as Greenville, but I think our brand could learn something from theirs. Some of the recent suggestions in this thread are a pretty good start.