I know this can be done with DCC to a decent degree of reliability, but fine-tuning the speed tables, etc., must take hours. Else one risks either telescoping or compressing the cars and -- oops! Stuff's on the floor.
Myself, I would be nervous the entire time doing this with DCC-equipped locomotives. I think my anxiety would be reduced greatly with RailPro, because of the advantages it provides for ease of consisting and the way it communicates with each locomotive.