Thanks for the detailed response!
About assignments: There was initially going to be a final fight after burning George's body. The idea was the graveyard introduces you to their abilities (if you assign someone weak to push the statue, for example, they'll fail, and someone stronger will do it instead. Likewise, the crypt is a test of courage.) in a harmless way. Then, in the final fight, if someone fails a task you assign to them, they die. The final fight got scrapped, though, so it defeated the purpose of that setup. With the exception of Brian. If you stress him out too much, he will leave the group before the farm, and wind up dead. That is assuming he survives the cemetery in the first place. It's a tough life for Brian.
There are a few things at the farm where who you have matters, but it's executed automatically. For example, one route involves shooting a window with a slingshot. Brian and Claire can do this, Satoshi and Andy will fail. But Tommy knows how good/bad of a shot his friends are, so it would be out of character to allow the player to potentially hand it to the worst shot. Another example is who helps with the fire, which is all done behind the scenes. In order for it to get done quickly enough for the fire team to be hidden before Scarlett arrives, you need to either give them the hatchet, or have Satoshi's fire expertise. If Scarlett arrives first, Link's companion will need to be fast enough to get some distance, meaning it must be Andy. Brian and Claire are too slow. Andy then additionally needs the walkman or slingshot to create a distraction to fully escape and hide.