yeah, it’s bugged… sometimes the “Arrange a Meeting” prestige objective won’t work, either
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Glad you got it working. On the original point, I believe this challenge is slightly bugged like others have pointed out. Whether it gets a fix in the future remains to be seen, but I think you just have to keep trying multiple burner phones during gameplay and it eventually counts towards the challenge 
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I have now managed to complete 8 freelancer missions in a row, it really helped to have a dart gun and play more cautiously (while caring less about the optional objectives, as well as caring less about avoiding cameras when not doing anything illegal) I still have very negative feelings about alerted territories cause the mechanic is just not great IMO.
One very funny thing is that the ‘poison target’ task can be used to cheese finale missions slightly. all you have to do is narrow it down to 2 suspects, which is not hard, and then shoot them both with a dart, the one that pops the task is your target. (though, I never did this, I legitimately narrowed it down to the correct target before i shot them)
there are also quite a few locations that just do not go great if you leave them till the leader mission.
Chongqing is the worst offender, all China targets (for me at least) are ICA facility members, and the facility is the hardest place on the map to go through without a guard disguise. and the place is so cramped it’s hard to avoid lookouts, on top of that the place is swarming with guards ready to shoot you at the slightest provocation.
Another pretty big offender is Hokkaido, as its door disguise gimmick means you might not be able to get to your target without using a disguise the lookouts can see through, plus the fact that it seems to always take place in the morgue, which is extremely cramped, means you’ll likely find out who your target is when they start running away.
Dartmoor is a bad map for freelancer in general. Starting at the main gate is pretty much a death sentence to any silent assassin or suit-only run unless you’re an expert or stupidly lucky. So, I hope you didn’t pick that as your prestige. It is also very hard to get a disguise in unless you clamber all the way up to Alexa’s room and knock out the guard for his disguise, but that’s a guard disguise. I tend to avoid any syndicates with Dartmoor as a locale.
I like the “Distract Target” objective… you can use it on all nine targets in the final showdown
While I agree Hokkaido and Chongqing are pretty bad maps for showdowns, Dartmoor is actually a very good one (it’s also great for SA / SO as there are many ways to get around without being seen, like pipes and secret doors).
If you start at the main gate you can just climb over the wall to your right and beeline to the windows near the butler’s office, nobody will see you. From there you only have to get the coin in the corridor near the kitchen to distract a guard (like the guy guarding the recorder) or servant (like the guy in the kitchen), hide their body in one of the many containers around the corridors (which can also be used to hide yourself if needed) and get their disguise to freely roam around.
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Not only is Dartmoor an excellent map for any stage of Freelancer, I would actually put Chongqing at #4 on my best locations for showdowns. When you use a phone to lure the leader to the sniper rooftop is a setup that doesn’t get much better.
In case anyone was wondering, the first three are: #1 Whittleton Creek, #2 Haven, #3 Dartmoor.
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Whittleton Creek is very free and open, it is the #1 place for showdowns.
Maybe I’m just unlucky in Dartmoor but when I try the wall hop strat I usually get spotted by the two guards on the entrance side of the bridge
I don’t usually use phones because it’s a hassle to get a hold of them. The only time I’ve gotten a phone was when I had already killed the target. The main issue I have with Dartmoor is that pretty much the entire map is hostile, this is also an issue with Colorado if you start on the water tower, you’re kind of screwed. Both of the nearest people are in pairs and will hear or see if you try to get them, your best bet is to sneak into the bathroom and turn on the sink to choke out whoever comes in, but there’s also a guy who can sometimes see you while you’re on the staircase, and if you get unlucky, guess you die. The best thing it has going is that there are 400 accident kills on the map.
It shouldn’t be an issue if you cross the river to the right and keep running towards the manor, you don’t even need to sneak.
IIRC the outside parts of Dartmoor are simply trespassing so you can just let a guard lead you towards the gate and bonk him when nobody’s looking. For Colorado: run towards the crate at the bottom of the stairs and hide there until everyone cools off (when non alerted you can even enter the room below from the window and get a free mechanic disguise before anyone can see you), then you can just lure a nearby guard and get his disguise.
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You don’t even have to hide:
I usually proceed from there by luring the guards in this room with the water. Get the point man disguise and from there it’s just a map like any other.
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For me, my go to levels for Freelancer, especially final showdowns, are either Mendoza, Whittleton Creek, Haven Island or Dartmoor. I also don’t mind Chongquing as long as it isn’t a showdown as like you said, I can become very problematic. I try and avoid Colorado and Hokkaido wherever possible. They both always cause me a headache. Mumbai is sometimes hit and miss as well, especially on Alerted territory.
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My favorite maps for Freelancer showdowns are Paris, New York, WC, Dartmoor, and Dubai.
- Because they are rather small (compared to SF, Miami, or Mumbai). You don’t have to travel the whole map to seek for head syndicates.
- Relatively open. Targets are reachable and go rarely into hostile area.
- Disguises are easily obtainable and somehow powerful for some of them. The auction staff disguise in Paris virtually allows access to the whole map, or the house staff in Dartmoor. In case of alerted location, there are civilian disguise, targets are not enforcer against them.
- Choose a syndicate where several go-to maps are present. This way, it gives you big chance of having a showdown map in a regular state (not alerted).
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Hokkaido isn’t completely awful. If the place isn’t alerted, all you need to do is make your way down to the morgue. More specifically, take out the guy in front of the video recorder there, stuff him in the nearby closet, and yoink his disguise. Just do not do any showdowns there.
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I’ve been playing Freelancer since launch and whether it’s Alerted or a Showdown, I still hate the level haha 
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Hokkaido and Bangkok are the bane of my existence in freelancer, Marrakesh can be tricky too if I am going for Silent Assassin.
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Oh god, I forgot about Bangkok as well. Another level I despise the life out of haha Colorado, Bangkok and Hokkaido are the worst for me!
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I was playing a bit of the main story campaign today and I forgot how much of a cool map Hawkes Bay was. I was thinking, it could easily be included as part of Freelancer either in the first or second part of the syndicate campaign where you only have to kill one target?
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I was playing Freelancer today on New York and I forgot how annoying it was to see 47’s tie appearing through his suit when you wear his signature suit with gloves and stand behind cover…….
I compared it to the Blood Money suit when playing the story mode and look how crisp the tie looks compared………….
The signature suit with gloves is ultimately my favourite suit (Blood Money close second), but it’s so annoying to see 47’s tie appearing through his suit during gameplay. I know it’s not the end of the world, but I know many people on here have picked up on this.
I hope it gets fixed one day! 
@Combatglue
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THIS, so goddamned much!
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I thought of you when I was posting this
I’ve noticed a few of the suits do this, but the signature suit with gloves is the most noticeable obviously due to 47’s red tie against the black suit.
I’ve tagged Combatglue in the previous post, so hopefully the devs can look at this sometime in the future
Hitman 2016 had the best signature suit. They messed it up in H2 and H3.
I mostly use the Absolution suit. I like the darker suit and the vivid red tie.