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This scenario is a cinch! The best way to win is to start at Memphis, building east across Tennessee. After connecting Memphis to Jackson, connecting to Dyersburg is not a bad idea, as it helps build the revenue base, and the player most likely cannot yet afford to connect to Nashville or Fayetteville. Buying some reasonably profitable industries in the beginning can also help. Just remember not to buy any industries that require raw materials except for textile mills, lumber mills, and paper mills.
It is best to connect to Nashville as soon as practical. Then making a few other connections, such as Paducah, Bowling Green, or Fayetteville is not a bad idea, nor is acquiring a few more industries.
Soon comes the point in the scenario where the banks will let you borrow money cheap for one year. This is when you make your move. Issue as many bonds as you can. Connect first to Knoxville, then to Charlotte. With whatever money is left, buy industries, just remember the guidelines I stated above. Once, after making the connection to Charlotte, I had a furniture factory lose $4 million in one year. Not that it mattered. The rest of the business was super profitable. Also at this point, buy as much stock as you can. Don't worry about margin calls.
After the connection with Charlotte is made, profits will skyrocket. Buy a few more industries while the going is good. These will get expensive quick. If there is a good place to build a textile mill, lumber mill, or paper mill, do it. As the profits keep rising, building more track becomes an exceptionally good investment. Go ahead and connect a lot of cities. Connect with the AI if you can. This is one scenario where I find it beneficial to let the AI live!
From that point on, just let the money roll in. Keep buying stock and expanding the business, just keeping in mind which industries to avoid. Before long you will start making money faster than you can spend it. Last time I had the gold medal, hard level, in 13 years.
Life is not fair, but it is still good.