I will start by saying there is a video guide with possibly a different method or better explanation of each achievement below, and I want to thank Maka91 for these videos.
So first up is getting a shotgun kill on a jump kicking cloaker. It's a stupid achievement and really annoying to get in reality. There's a small frame from them jump kicking and whoever the target is being downed. The easiest heist to do this on is probably Watch Dogs day 1, as there are some easy to find sewer grates. Once the police assault starts, just watch these grates until a cloaker pops out, then try to get his attention or let the AI do so, and try to time your shots just right, as you have a small window for this.
The best weapon to use in my opinion is The Judge, it's an insanely powerful secondary shotgun and can fire pretty fast too.
Okay, so the next achievement requires a triple kill with a single bullet of a sniper rifle. There aren't many regular opportunities to do this, and it's easier to find a setup spot than wait on pure luck. I would suggest the Thanatos .50 cal if you're a high enough level to use it, as it does more than enough damage to kill. If not, the Nagant Sniper Rifle should do. So the general method here will involve the regular bank heists. You want to alert the police and hold out for the first assault wave. Now when looking at the bank from the front, you'll see a gate on the right, go through and go to the back here and turn around, the rooftop now to your right will have 3 cops rappel down from it at the START of the 2nd assault wave, so get ready to line up the shot.
I personally did this on Normal, but if it's not working for you, then you may need to up the difficulty for them all to drop down.
The next 2 achievements can be done together, but will require a little bit of patience to get. You can do it 2 ways, either go loud on a heist like Jewelry store and wait for cops to build up (turn off AI and do it on a lower difficulty too). The other way would be to start Watchdogs on a lower difficulty and bring the Buzzsaw and the Saw with you. You can saw through the bottom of the van here and if you're lucky, you will have anywhere up to 12 cops here. Spray the Buzzsaw without releasing the trigger, and if you killed 10 without releasing the trigger and in less than 10 seconds, you'll unlock:
This next achievement you can do in the same spot mentioned above. Bring the GL-40 Grenade Launcher to day 1 of Watchdogs, and once the doors open, fire a shot and you should easily kill 4 at once to unlock:
Next, equip the Telescopic Baton melee weapon. All you need to do for this achievement is melee a shield enemy to death with it, so just run circles around them so you can hit their back.
Finally, equip your favourite melee weapon, as we'll need to kill 50 enemies in a heist using only melee weapons. This means you can't kill an enemy with anything else in your arsenal, so keep track of how many you kill and finish the heist when you're a little over just to be safe. This would be easiest on something like the Ukranian Job or Jewelry store.
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