Sorry to play devils advocate but in this scenario we don't know if Bob bought high.. I understand what you're saying but a lot of homeowners looking to sell these days may have paid a fraction of what their home is worth and have to rely on comparables to dictate true market value.
That's the fucked up thing about RE. It's not gold where you can look up what an oz is worth. It is worth what someone is willing to pay.. and we're also talking about tax free gains if it is your primary residence.. 400k cash is a lot of dough towards Bob's retirement/well being.
Anyway, enough about Bob