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...
This is what we are suggesting, his winnings plus the over betting amount is the most sensible conclusion to it.