The city offers much to love. So much to love. Almost too much to love. Sometimes San Francisco’s allure shines so bright that areas of concern, of which there are many, go neglected.

One example would be McCoppin Hub, a public plaza built out of a dead-end street near the Octavia offramp. What began as a good intention turned into a lackluster experience. No cafes, shops, or regular activities resulted in a space that is now unseemly, fenced off permanently with an foreboding gate.

This is what it used to look like. This is what it looks like now. Not fun.

And with that, what are some of the other biggest mistakes, or wasted opportunities, San Francisco has made or passed up when it comes to urban design. (The glorious Vaillancourt Fountain is a cheap and easy shot—we challenge you to dig a little bit deeper.)