1. Why did 50 Blessings order Richter to assassinate Jacket in Hotline 1? It makes no sence. The chapter itself (Deadline) is strange too. That phonecall is very different from all others, with that "Ahem" and "click click click click" - it seems like the caller was very nervous, and unable to hang up. It's like he was calling for the first time. My best guess (although streched out) is that it was mafia's trap. They call Jacket, pretending to be 50 Blessings, and send him away on a mission. Meanwhile, they do the same with Richter (who also thinks he does 50 Blessing task). Two proofs for this: Jakes story in Hotline 2 (I'll get to it in a bit) and court trial in Hotline 2, when police chief states that "the tape was removed from answering machine", but "the calls were traced to russian night club", although there is not a single reason why they would come from there. But once again, this kinda seems streched out.
There was no point in assassinating Jacket. Why they wanted Helmet out I can get (he's still alive, tho), but Jacket? He was suffering hallucinations from the very beginning (saw Beard everywhere he went, although Beard was long dead by the time Hotline 1 events were taking place). Maybe he was demented since the war - who knows. It's not like illusions made his combat perfomance worse. And he wasn't insane at all - he actually explained his actions to the lawyer during court trial in Hotline 2. In fact, I believe he followed 50 Blessings orders with no questions asked because he had his own motives to kill russians. He was on his quest for vengeance for his (only?) friend Beard. That's why he didn't stop even when there were no more phone calls. That's why he kept his polaroid photo with him, and dropped it at the end of Hotline 1. He aknowledged his illusions, he knew that he saw dead people, and that Beard was one of them too. He wasn't following orders, he was merely using intel provided by 50 Blessings.
I know that in Martin's movie Jacket is shown as "fucked up in the head", but it's not like the movie was anywhere near real Hotline 1 events.
2. Jake's storyline I don't get. He was receiving calls from different operators than Jacket, and he was supposed to die during a failed mission - we can clearly see his corpse in chapter 10 of Hotline 1. But in Hotline 2 he is killed by an operator for no real reason. I mean - ok, so he asked questions and had an AWESOME PLAN OLOL - obviously, Jake was dumb as wood. His dumbness, much like Jacket's broken mind, is not reason enough to kill him. He does the job, and he does it good. Unless those operators were not really 50 Blessings, but just imposters. Judging by Petrov's confession in Hotline 2, russians were able to catch and interrogate several masked vigilantes during Hotline 1 events, so they could possibly try to imitate 50 Blessings themselves. To fight the competition, maybe? Like the Colombians? Is that the reason they killed Jake - because he wanted to kill "russians only"?
3. Final chapter of Hotline 2, The Apocalypse. During a drug trip russian boss goes KILLING SPREE, and we can clearly see how he kills Mark, then Cory, THEN TONY WITH A FUCKING SHOTGUN, then Ash&Alex. Then yolo-jumps from the roof gloriously (best chapter of the game). But Tony was ALIVE, and even more so - UNHARMED - when Pardo found him in the building. And for some forsaken reason, corpses of Mark and Corey were laying in the same fucking room. It's not like the SWAT moved them - they were too afraid to enter the damn room before Pardo arrived. What the actual fuck? Some random russian mobster found the masked corpses, dragged them in one room, took Tony's mask, put it on, and... wait, what?
Seriously, how did Tony survived and why were the corpses together? They were all:
a) clearing different floors on their way to the roof, separately;
b) killed by rus boss in different places of the building.
4. What exactly is Pardo's problem? He randomly kills mobsters because... why? I figured out that it's related to FAME somehow, but his actions don't make too much sence. The only theory that seems to fit is he does all the mass-murders, so the other murders would fade on the overall picture. So all the maniacs, serial killers, Jacket fans, and other fame-craving criminals will give up hope, and the press will lose interest to small-time massacres. It kinda worked with The Fans (they only got a few minutes on TV after all the killing they did), but it's STILL a REALLY stupid way to achive this goal. Besides, he reccomends Evan to write about Miami Mutilator at some point, whch contradicts this motive a bit. The game gives a few hints that Pardo IS actually the Mutilator, but I don't really think so. Mutilator kills civilians, while Pardo aims only for criminals.
5. One more crazy question about Pardo. The punching bag in his apartment, the face features, the eyes... Is he some relative to russian boss? A brother? A son? Is this the reason he hates the mob, but still has strong connections with russians? Then why isn't there more clues to it in the game?
6. Awright, so WHO THE FUCK is Richard? "I am the opposite of why you are writing your book". Maybe I missed something in Evan's story, or maybe I'm just stupid. Why is Evan writing his book? Except for the money and almost unnatural interest in Hotline 1 events, I don't know. What's the opposite to it - I don't know either. Ok, so Richard was obviously a part of Jacket's broken mind during Hotline 1 events, but in Hotline 2 he is much more. Not some kind of group hallucination, and not a simple narrator either. During Hotline 1 he asked four questions, the last two of them remained unanswed for me (inb4: hallucinations). During Hotline 2 there are several moments where the game stresses out of importance of Richard's personality. Who is this damn rooster?