Fastest Way to Rig/Weight Paint a Neck/Collar Area?

Hey everyone, I’m wondering if there’s a fast way to rig/weight paint a neck/collar area? The problem I’m having is the head of my character is a separate object from the shirt and there are lots of intersections going on depending on how each arm rotates or also depending on the direction that the head moves. Since there’s a crazy amount of possibilities when it comes to what direction my character could move that would cause an intersection, I’m wondering if there’s a trick to doing this quickly. I do know what to do and how to weight paint, but I’m still new to Blender and I’m wondering if there are any tricks to speeding up weight painting and preventing the neck from intersecting through the collar in this particular area. Thanks in advance.