How do I win a title?
You have to be one of the top three haulers on the server of a specific good the day before.
You can win a title for Money - this requires you having an income in the Top 3 of all the Players on that server.
As above - the Goods titles require you to have delivered enough tonnage of the Goods from Daily reset to Daily reset to be in the Top 3 haulers on the Server.
And for passengers - you need to deliver the most passengers.
For the money titles - the best advice I can give is that you have the strongest trains of that Era and you purchase licenses relevant to the Goods you are hauling. Integration or Passenger hauling is one of the best ways to have a high income turnover.
For the Goods titles - If I am running for titles I personally switch between different cities to benefit from the lower wait times, and then go back once the Wait times are lower as this allows me to deliver more tonnage per hour.
For the Passenger titles - you are looking for the shortest journey of the Passengers and you would be best to find this manually as the timetable calculator gives you the best incomes and not the best times.
Hope this helps!