Train Valley 2

While any expansive level where you start with a bit of cash should do the trick, I’d argue it gets easier on levels from the ‘Passenger Flow’ DLC – because you can call the next passenger train [the Plus icon in the top middle of the screen] before you started/delivered the first, which plays into the “having money” issue. ;)

So, since you can call the next passenger train before you have started the first, do that twice or as often as is possible with the number of stations. Then, look which of the new trains has the shortest distance to its destination. Build those tracks first, but don’t start the train just yet.

Then, build tracks from your first train into a looped bit of track. Start that train and have it loop until the end of the level.
You’ll now potentially be out of money or at least close to it. Good thing you built the other tracks, right? Deliver your additional train now and you should get enough money to play the rest of the level as normal.

Once every other train is delivered, free the first train from its torment and the achievement should unlock. You don’t need to get all fives stars on the level.

See this screenshot for a potential set-up from the beginning of the first ‘Passenger Flow’ level: https://imgur.com/a/nhBF8Ih