Given that the maximum win is $2000 and that the maximum bet whilst maintaining house edge (in this particular instance) is $55.55, shouldn't yahoo get $2000 + ($323.949 - $55.55)?
And check out this scenario which complicates things in regards to betting:
Suppose someone bets $1000 on red.
It would be -ev to bet on any other option that pays out red numbers.

But depending on the outcome, both sides will have differing arguments...