Orchestrated?
Maybe to the point where Orlando & his associates said 'let's kill this nigga', but apart from that, there wasn't much organised about it.
Like I said the shooting was actually sloppy - as you mentioned, the DR entourage around, there was nothing orchestrated here.
As for it's strangeness (like 'Pac not wearing his vest) it's coincedence/luck. Just like 'Pac could've easily died in NY when he was shot.