In looking at (even) the corrected rules - you start with 3 cards up, but then in the 1585 year you do not turn up an additional 3? (Or any for that matter...) Seems like if you are playing with 4-5 people some folks are not going to get in on a contract at all. Could someone mention the rationale behind this?
We plan to play tonight (Christmas eve) and I want to be sure I understand this part of the rules clearly. the rationale will help me understand and explain the possible screwage factor. My guess is that once the ships sail east, all you do is pick up contracts in Phase 3, so you are best to invest in sailors and merchants first and then decide on contracts afterwards...
And with a closing thought - I can't see ANYONE wanting to pick 1585 as a completion year for a contract - seems insane!
Hopefully someone more knowledgeable will come along and answer this question. The only thing I can think of is that the 4th and 5th player at least have the option of stealing a contract from the first three players by proposing to complete it by an earlier year. Since this question is pretty old, maybe you've played a bunch since then, and can shed more light on it than me.
An old question... but perhaps I can still help future players with this one.
You start with three contracts... and you'll have to wait until 1588 for extra ones but, so indeed, only three players can take a contract but...
In the games I've played so far, I noticed that players who just join in on a ship, without having the pressure of a running contract and help (or boycot) with a precious cargo to return to Middelburg until 1588... can take a very lucrative contract the moment it comes up, with already the necessary goods in their holds.
Plus... they don't have the chance not to uphold their contracts.
They also have an extra turn to fill up the ships, which can lead to more chances to steer contract holders astray, to other ports, to nab the contract holders' goods before they can get them and cash in during the trade phase. I am eager to try this with four or five.