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The Most Wanted missions requires 30 criminals to be killed via the police computers.
The Strangers missions add up to 16 because of the multiple encounters. Note that Brian has three encounters while Sara, Pathos, Marnie and Eddie have two encounters. All other required strangers only have one encounter.
In terms of going out with friends, I am pretty sure that only pool, darts and bowling are required to be finished the entire way through. In terms of their activities ...
for Brucie: boating, bowling, drinking, eating, heli-ride, cabaret/comedy show or strip show
for Little Jacob: pool, drinking, darts, eating, cabaret/comedy show or strip show
for [Patrick]: pool, drinking, darts, bowling, cabaret/comedy show or stirp show
The conditions of Roman and Dwayne should not affect this, I believe, and neither should any decisions made within the main campaign.