I reccomend putting your game settings like this before starting the achievement

First of all, to get the achievement the easiest way for me was to go from sawmill, to vlad's shop and then the restaurant.


So when you get to sawmill, get out of your car and handcuff the 2 NPC'S there



After doing so, walk to vlad's shop while facing backwards to where youre going so youre always facing the NPCS youre trying to come with you

(Btw if one of them starts screaming it means theyre about to run away, so go to them and click the ''follow me'' button)

After walking all the way to vlad's shop you need to handcuff this NPC


And again walk backwards to the restaurant while facing the NPCS, and when you get there just handcuff the first 2 people you see



and after that you should be done!! and if not one of them mostlikely ran away so try to handcuff someone else at the restaurant, if it doenst work restart the run

If you still dont understand much, i made a youtube video of me getting the achievement so just follow what i do on it

and thats it, if you have any questions feel free to ask