Okay.
I was looking at the Vegas O/U for team wins this year, they have the Phils at 88.5 and the Cubs at 87.5. So, in theory, I should give you a game. However, I don't think I should be yielding games given that the Phillies play in the East and the Cubbies play in the Central.
As for the modifications to the 2nd bet, my thought is that we allow you to make a change once in each category, with the deadline for changes being the first game after the All-Star break. That will prevent the situation that occured last year, where there were categories that were uncontested due to injuries, lack of playing time, etc. However, if you make a change, the change only counts going forward. For instance, if I picked Victorino for steals for the Phillies, and 6 weeks in, Victorino has 5 steals and Rollins has 12, if I make a change, I still only have 5 steals, and then I get however many bases Rollins steals from that point on. So if he ends up with 30, my total for betting purposes would be 23 - Victorino's 5, plus the 18 Rollins had after I switched.
I'd also get rid of outfield assists as a category, and instead have the tie go to the person who made the fewest changes to their original picks.