No idea about the ship maintenance. It would be logical that an older ship needs more maintenance (in the sense of "more often"), seeing that the prices in the game for used ships are so much lower for old ships.
I like coal from Sydney - iron from Tokyo (or what was the "grey" metal again?), doesn't run out if you don't use too large ships.
Also nice: coal from Sydney - machinery (the green things) from Tokyo - Hong Kong. Then back to Sydney with whatever Hong Kong has available.
Quite profitable: machinery or cars from Western European harbours to West Africa, then haul cotton or fruits back. Just change African ports quite often to keep some availability.
Wood from Halifax to some Eastern USA harbours, take iron on the way back.
There's also a route between 2 Eastern USA harbours that involves the yellow-grey and red metals (don't remember by heart what those are called) one way, and iron the other way.
Very profitable using bulk freighters: rice from Brazil to Hamburg (Hamburg pays quite a high price for rice). You can switch to coffee and/or cocoa whenever the rice availability would be too low.
Lineseed oil (or something to that extent) from Brazil to Rotterdam. The same oil also works well from Chinese ports to Sydney.
Rice from China to some of the ports North of Australia, then take oil from there to Sydney.
Passenger ships are awesome once you manage to buy them...
You can easily get over 10-15 million income from 1 trip. Just make sure to transport passengers over the longest possible distance: income = # passengers * distance
Maintenance costs and times are huge though, so keep some other ships to keep your cash flow steady during these maintenance intervals.
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A sickened, sensitive shadow writhing in hands that are not hands, and whirled blindly past ghastly midnights of rotting creation (Nyarlathotep, H.P. Lovecraft)
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