If you want to win championships, building a championship team is the last thing you do. The first thing you do is get investors on board and start building infrastructure and brand recognition. The whole notion that "anything can happen" on the field of play is a myth in baseball. It's a statistical inevitability that (in an uncapped, lightly regulated league) big cities will win and smaller ones lose. Which is why NYC is bloated with championships while some very old teams have perhaps one or two.
I agree with a lot of what your saying. Money eases the path to championships. It's true. But it doesn't guarantee it. The guys on the field still have to make the plays. The pitchers have to throw strikes and the hitters have to hit in the clutch. The Yankees have won an awful lot of Titles, but they don't win every single one, though they probably should on paper.
IMO, the NFL has done a much better job than any of the other leagues of creating a system that levels the playing field for all franchises. Just look at Green Bay. They not only compete, but routinely make the playoffs and they're probably the smallest city in the country to host a major sporting team.