That is my first post. After finishing all of the three acts of Doomsday Heist, I started to wonder when does this everything take place. As we know, game developers in recent updates cared a little bit less about the timeline.
Up until Import/Export update everything was in order - events of Online take place before Michael and Franklin meet each other in Jimmy's car. We stole cars for nice profit. Some of the collections were requested by characters that become dead at some point in Story Mode (like Jay Norris). Similarly with original Heists Update from 2015 - the Humane Raid takes place before F. M. and T. storm the same location for FIB. Contact missions from Martin Madrazo are finished by driving to his yet undamaged mansion.
With GunRunning things became complicated - Vehicle Work involving chasing rogue agent in Weaponized Tampa starts with a statement from Agent 14: "It is 2017". Same with Smugglers' Run - Ron says that Trevor has gone full Vinewood (probably a nod towards Steven Ogg and his role in The Walking Dead). Therefore starting with first major update in 2017 (the Gunrunning), events of Online are contemporary.
With all this high tech combat stuff in Doomsday Heist Update, one would that it also happens in 2017. But there are several dialogue lines which might lead to different conclusions. This is my list of doubts that arose while playing Doomsday Heist:
1) Lester never mentions the days he was working with our well known trio on the Union Depository score - yet somehow he refers Nico (whom he does not know) and ULP agent (whom he is about to meet for the first time) doing wet work back in Liberty City (Three Leaf Clover).
2) United Liberty Paper is alive - he can be easily killed in Story Mode as he is pretty much at the worst end of the barrel.
3) Merryweather still present in Los Santos - after finishing Story Mode they stated that they ceased all their operations on US soil. On the other hand, we still fight them in Gunrunning selling missions (so that's not really a proof of anything).
4) Lester wanting to come back to simple bank robberies - is it really nod towards all these players who don't really appreciate the military content? Maybe it means that all the scores in Story Mode haven't yet happened?
5) Lester's statement before Act III Finale: "we won't have to rob Union Deposit - IAA will give us the keys!" - if Doomsday Scenario takes place in 2017, then Lester already has his cut from 2013 UD score. Why would he then be so keen on robbing it again? His excitement whilst mentioning UD makes me think he has not yet contacted the people willing to pull off this kind of job.
What do you guys think?