I'm not familiar with the other 8 Iron Rules, but this one is definitely good. As per the example, self-depreciation to that extent is akin to pleading insanity.
I'm sure there are some women out there that would be partial to a man's self depreciation - perhaps the type that are after a broken wus. But for most self respecting women, I suspect it would equate to a huge turn off.
On the otherhand, how should men receive self-depreciating women? Is there more tolerance in this respect?