How about we can hire a Mercenary Pirate for a day. His function would be to sneak aboard another ship and tell the level of their hull or maybe even be able to temporarily damage their hull before the attack or even steal a small amount of gold and you would not be able to attack...
This Mercenary could also be a permanent upgrade added to the list of upgrades at towns. His (or her) skill level could be upgraded for a fee, getting more expensive each time just like other upgrades (ship, hull, etc.)
Of course you would also have the option to purchase (or temporarily hire for the day) a lookout to defend against such a culprit...
It sounds along the lines of observation / navigation but instead of seeing a colored dot, you would know what you are getting yourself in to. That is, of course, if your Mercenary gets past the other persons lookout(s).
This could also increase / decrease your fame level based on your success / failure... Or even a new addition to piracy points...
Just some thoughts...
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