I'm not sure you're understanding the concept. The Ricketts family bought the Cubs. He pays employees and charges customers. When the books are balanced, they/the Cubs make a lot of money. They don't really pay to lose. HBD owners drop $20 on a team. When they lose, their best hope is to get a $4 credit. They're paying $16 to lose.
Depends on the situation/settings. If you have both set to "ANY", SIMMY will use the best pitcher.