Playing through the entire game only got me about 60% progress towards this achievement. Then i discovered a much faster way to cause 500000$ of damage. When you found at least 45 of the hidden blue books in story mode, you unlock challenge number nine. The objective is to cause as much damage as you can. So here is what you do: start the challenge and run towards the big desk on left side, destroy it then you restart the challenge, that's it. The desk is worth an entire 5000$. So using this method will earn you that achievement very fast.