I got around to trying this today, and it's certainly challenging enough for me! Although I should note that I played a couple orders of magnitude more II than III, so my play is sure to be sub-optimal.



First time around I decided to start in Florida. I guess because the terrain was flat? Long story short, I didn't make any money. Any that I did make in a good economy would be canceled out in a bad economy.



Second try I decided to try to fix that up by buying a lot of industry. So I bought some oil derricks, sugar and fruit plantations, and a logging camp over the first 15 years of the game. That gave me about $600K/year in profits, which I then poured into a Lone Star electric railroad. Which was all well and good, until around 1925 I realized that I had no chance of winning, and worse than that, my rail operations were unprofitable once track maintenance was factored in - my industry was subsidizing them, and I was making less than 10 years ago. I played on until around 1934, but profits were not forthcoming.



Third try, I decided to go east coast, linking DC to Richmond. Thanks in part to some dairy processing, this was mildly profitable, enough to enable to to issue bonds to fund a gambit - building a textile manufactury in Richmond, and hauling cotton from eastern VA/NC there. This paid off handsomely, and several years later I was able to expand south to Wilmington and Columbia, enabling the purchase of a lumber yard and a weapons factory that I supplied along the way. Owning industries and then supplying them by rail seems to be a more complementary strategy than what I had going on in Texas, and having 3-city segments of passenger traffic, with a few restaurants/hotels/taverns as well, is helping make express traffic profitable for the first time.



I still doubt I'll make NYC to San Fran by 1930, as it's 1914 and I'm still only in 3 states and D.C. (and I hadn't realized till re-reading the OP that I needed St. Louis too... had been planning a southern route). But it's a good scenario, I like the events and the additional non-starred towns, and it is nice to be making progress each time.



Edit: Well, I surprised myself. The profits kept rolling in, and I made good extensions to GA, AL, TN, up to St. L, and through AR to TX. Also bought up an unprofitable oil refinery in Memphis and brought in crude to make a pretty penny. Although I'd racked up loans with my quick expansion - reaching the $10M limit - from 1924 through 1929 I was able to pay them down to $5M, though my expansion slowed down, going only from Dallas to Lubbock in that time.



Then I took out the max again, waited for the depression to hit, and built all the way from Lubbock to San Fran at once, with a couple hundred thousand to spare. This did mean building some less-than-ideal track - notably a 15% grade in Arizona and going up and over the Tehachapi Mountains instead of tunneling through - but saved the possibility of a bronze or silver medal. I'll probably go back and make those lines more sane as I have money to build stations along the way. Including, of course, a station in Albuquerque, which my line goes just south of currently.



Edit 2: I should also note that my weapons industry fell apart after the Great War. Around 1922 I realized my industry profits were lower than would be accounted for due to the usual economic cycle, and sure enough, I was losing almost $250K a year on my weapons factory. Which makes sense historically, and was kind of cool (except for the bottom line). Made for a good example of when selling an industry may make sense, and that's what I did!

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