The win conditions seem out of kilter. There are two win conditions - connect all the major cities AND have 250 million in cash. The weird thing is these seem to be way way different in difficulty. Connecting the cities is pretty easy, in fact perhaps too easy, the game can be pretty short if you get lucky cards early, but getting 250 million in cash takes a long time and becomes a boring grind. It seems like a better win condition would be something like connecting a major city is worth 40 million in victory points, cash on hand is worth victory points, try to reach 300 million victory points.
Perhaps most broken is that there's just almost no interaction between the players. It seems to be one of a classic type of bad board game which you basically play in solitaire, and it's just a race to see which solitaire player wins first. That is a horrible horrible type of board game. I also don't see any real deep strategy, yes there is planning, but I can't imagine ever playing against someone and being amused by the clever trick they use against me. (basically the only interaction with other players I see is running track to block them ; yes there are optional rule additions that add a bit more interaction, such as open contracts and leaving dropped cargo in towns, but even that is pretty minimal).
I've had a hankering to play good board games recently and have been pretty disappointed. Carcassone is decent and actually has some interesting play (almost all the interaction and complex strategy is about farms), but it's just too simple; I think it's a great kids game. Settlers is a really mediocre game; almost all the real thinking is just in the placement phase, and then the actual play is pretty rote and becomes just tedious after you play a lot. I supposed Settlers is more interesting if you really play the metagame of influencing people to make them trade with you advantageously (just like Monopoly is only an interesting game if you play the metagame), but I'm not a big fan of political metagame as a form of strategy.
So many of the "sophisticated" board games that you see are just a bunch of over-complicated rules that surround a play dynamic that's not very deep. You spend hours reading the manual and figuring out how to play, and then when you actually "get it", you discover the game is trivial (by "trivial" I mean a very smart person will know the correct move in each situation).
I know I should just play Chess or Poker or Go or something real, but it seems like there should be a better middle ground of games that are "fun" and not so serious as those, but also have something actually interesting and challenging to think about during play.