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The only thing I can think of is maybe it’s because I’m doing it on a created contract rather than on “The Finish Line” proper mission.
Ok someone in YouTube comments confirmed this is bugged for some people in create a contract. Works in the proper Miami mission though. I’m just not trying to drag one of the main targets from that all through the map to the wood chipper lol
It probably was because you tried it in Create a Contract. I don't know if you can unlock any challenges whatsoever in contract creator mode and I know for a fact that many challenges are restricted on the Contracts versions of missions. (you can see which are up for grabs by viewing the challenge menu)
I just did all of these challenges easily in about 5 minutes
Started in the driver lounge (above the garages), took the bags of sugar from the bar (where you start) and the kitchen (across the hall), walked down into the tunnels to knock out the flamingo (it has to be the blue shirt one looking for the keys), walked back out to the thwack stand and picked up the picture of the flamingo. (narcissis)
Then crossed under the tunnel near the main entrance, grabbed the diggerido, Shot sierra in her car from the walkway before going into the building and the aquarium to toss in the sugar (triggered no problem). Then went upstairs, knocked out robert knox and dragged him down the stairs and out to the woodchipper, popping guards in the head all the way down.
Quick and dirty, all challenges complete
If you struggle to shoot the guards, you could switch to the florida man and lure him outside, then knock him out outside, there's less people to kill and you can drag him right down the water line to the wood chipper
no need for that. you can make the guy standing around by the water (or Ted the military guy) your target in create a contract, pacify with digeridoo & put in woodchipper. the only challenge that doesn't pop in created contracts is the sugar one.
*shrug* i had them all done in about the amount of time it would take to create a pointless contract
Sometimes I want to make everything clean and finish all missions I start, but sometimes I just want to get the challenges/costumes and take the easy way out.
Same, only I did my own contract on the guy standing right by the back entrance to the woodchipper. was really fast to create in this case as only 1 target and you can start right there