This topic is what really depresses me about this season. I don't feel like we're all that much closer to contending than we were at this time last year. We've added some talent but at the expense of a decent chunk of our payroll flexibility (assuming there's a cap to how the payroll we can operate at). There are promising prospects but none that look like superstar middle of the order bats. With Jed's conservative approach to building a team, there's not a great avenue to get a batter like that via FA either.
What continues to frustrate me is not using our significant resource advantage to dominate this division. Being a big market doesn't automatically make you the best team every year but the metro population of Chicago dwarfs the other 4 cities in our division.
Metro population of Chicago - 9.4 million
Metro population of Cincinnati, St. Louis, Pittsburgh and Milwaukee COMBINED - 8.6 million
Even if you consider the White Sox and split Chicago's population in half, the remainder is still more than double any other city in the division except St. Louis (4.7m for Chicago vs. 2.8m for St. Louis). Yet the Cubs have won roughly 21% of the NL Central titles since the division was created and have finished in 5th or 6th almost twice as many times (11 times) as they've finished in 1st (6 times).
Again, having a financial advantage isn't going to guarantee you win every year, but when you have such a giant financial advantage, winning on average 1 out of every 5 years is really poor.