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Natural Selection - Eliminate 10 Syndicate Leaders with natural/crafted poisons.
Don't Lick Me - Eliminate 25 Syndicate Leaders with Poison.
With there being 18 missions every campaign, for 4 of them I will be forced to use the least efficient assassination method contingent on RNG:
1) they need to consume food/drink,
2} I will need to ensure nobody else consume the food/drink,
3) I will need to ensure Ambrose Island is the showdown map each time.
3a) they need to hang around the bar.
Alternatively, I could use a Lethal Syringe, but the gear drop isn't ensured.
Employee of the Year - Eliminate 500 Syndicate Leaders.
That's over a month of my life gone. I'd much rather cheat.
A Necklace to Die For - Strangle 10 Syndicate Leaders wearing a necklace.
Completely dependent on RNG spawning them in with a necklace, RNG spawning them with an assassin, RNG spawning them in a crowded area, and it has to be the leader - nobody else.
High in Fiber - Eliminate 25 Syndicate Leaders with Fibre Wire.
Fibre Wire is detrimental. It gets the leader closer to a dumping spot when you're in a nip, but ranged methods are far more consistent (a running theme for all my most hated challenges).
The only challenge I loved was Return to Sender - Eliminate a Syndicate Leader with an item retrieved from a Suspect. "Haha, Leader go boom
Note: Autumn Harvest was my first map achievement. What? I like Arms Trafficking! I like sniping from the water tower even more!
Oh I guarantee You it will take more than a month to complete. If 23 campaigns I completed so far took me almost 3 months (and that means 92 leaders killed without cheesing), it will take at least a year to complete.
Like I quoted, you would need to complete 125 campaigns to get 500 leaders killed. Without cheesing.
You could do it faster by killing them and then failing the showdown. So always just two missions before the next showdown
Adapt to what the game gives you. If a leader spawns with a necklace then take fiberwire and get double points for High In Fiber and A Necklace to Die For. If they are dehydrated then bring some lethal poison or pick a map like Mendoza where you can craft a lethal poison to get double count for Don't Lick Me and Natural Selection. For Burning Man just knock out a suspect in a remote area, use the phone and watch as all the suspects come to you so you can just stack 5 or 6 of them in a pile and burn them all at once. It's really not that difficult. Bonus points for getting credit toward Let The Chips Fall Where They May and Prank Caller by doing this strat.