Sid Meyers Railroad Tycoon and Colonization
I've still played the PC version occasionally on Dosbox. Despite its faults and aging, the original still seems to have something unique to it that other newer transport business games lack. Some of that is probably nostalgia but I think there's something else to it as well.
Some of its bugs and limitations can be fairly annoying, and at some point I toyed with the idea of making a rewritten clone with those issues fixed kind of akin to what OpenXCom has done, but I was never able to gather the motivation to do the hard work of reverse engineering the gameplay mechanics etc.
The ones that I've found more annoying than amusing are things such as:
- The maximum cash of 30M (10M or something in the deluxe edition), at which point you can no longer make a profit without jumping through hoops
- Not a bug, but the limits on the number of trains and stations combine poorly with the above
- If you have multiple rate wars at the same time, you only get the periodic status report on one of them, forcing you to play blind in the other ones
- In the deluxe edition, I'm pretty sure there's an overflow or some other kind of a bug in the final score calculation that has significantly dropped my final scores on multiple occasions
One that was more amusing was that I think if you bought control of two if the other companies, you were also able to access the third one (e.g. to transfer money to yourself) by using a bug in the broker menu.