When should I start Smen?

At what stage of the game would you recommend starting the “Smen” quest? I shamelessly created a second account for this purpose, and now I’m wondering when is the best time to start in order to experience the full range of emotions and complete it as quickly and… uh… comfortably as possible? Should I become a person of some importance at first? Buy a ship? Complete an ambition?

Just start is ASAP. There’s a section where the easiest way to advance is to spend lots of real-time - you can get one point of SMEN each week from the marsh-mired/unaccountably peckish combo, and that’s the easiest way of advancing a bunch of those early levels.

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You could start it anytime and progress until a certain point. At this point SMEN requires of your character to posses almost no items (except of certain types). So you are forced to convert all accumulated value (and more importantly diversity) of resources into those items (with some loss due to conversion). So the best timing to overcome this ordeal is very early (because character is very poor) or after big purchase on which you spend almost all your riches (like Cider, Hellworm, or maybe Over/Ubergoat for more casual players).
You are asking about ship and POSI, so you are very early, start the SMEN and enjoy the pain. I recommend not rushing it, after all it’s one of the best stories in this game IMO.

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