Why does Negan have to do his own communications? I mean if the Saviors are such a large group of people you'd think the top boss would have more important things than handling the "amber" alerts (or orange alerts or whatever) whenever someone escapes from the Sanctuary. Negan would be a much more believable threat if he did have a better fleshed out organization. Otherwise if you kill him the whole thing falls apart. But if you see he has competent seconds-in-command then the evil would continue. So far we have only seen dumb thugs. Nobody with any real brains.
Also, with all those people why weren't there more guards on duty except Fat Joey? You'd think there would have been more gates between Daryl and freedom. Both to keep the walkers out and the humans in.so he'd have been shot dead long before he got that bike out on the road.

What exactly makes you think they set it up for our group? Both Hilltop and The Kingdom travel that way along with possibly other survivors.

How did they know enough in advance to set up that elaborate trap for them
The Saviors (Negan) not only cover their arses, but prepare for any 'in case of' situation. Season6 Ep16 showed forethought/planning.
"You are entitled to your informed opinion. No one is entitled to be ignorant."-Harlan Ellison