One simple tip: Do this in the campaign. It counts. I tried "the Automobile" scenario about 10 times, save-scumming, difficulty adjusting, all sorts of tricks, got all golds on all objectives and still couldn't get president rating. I'm sure it's possible but I'm pretty decent at this game and just couldn't manage it. This is almost trivial on the campaign.
Basic tips for the campaign mission: You want to shoot for gold on all objectives, which is finish all tasks in <50% of the allotted time.
Focus a lot on Toledo from outset, and build to other cities for mail/passenger express routes (money). You'll need to bury Toledo in freight deliveries; my preference is to use warehouses, one to the northwest and one to the southwest. Feed your industries especially. Buy the museum in Toledo when it's available.
Lumber was tricky; I grabbed wood from the southern warehouse, turned it into lumber in Toledo, then direct delivered (through Chicago) to Rock Island. You might be able to drop a lumber mill industry in Chicago or Madison but it felt like a distraction in my playthrough.
Delivering passengers to Omaha is straightforward, just make sure you have a single track that goes from Toledo to Omaha and make the train passenger only. I recommend setting a minimum number of cars (I did 4) to make sure you're not spending a bunch of time going back and forth. Feel free to double your tracks and make them directional to have multiple tracks/trains, but again, felt like a distraction to do this and it wasn't necessary to gold the objective.
I didn't have an issues with money so buying out a competitor (I did both) was fairly trivial. Exploit an analyst freelancer to drop a competitor's stock price if one appears, it will save you a lot of money.