Cloth Simulation Fluffy Pillow and Quilt

Hey guys…
I’ll start off by saying this is for an animation… Otherwise, I would sculpt everything as per usual. Here’s my issue.
I need a realistic (stylized) animation of my character interacting with this bed.
To clear the picture which is surely forming in your mind, he’s a 12 yo, weeping, as he just lost his father.
Question #1
Now, I need the cover to wrinkle when he moves on it, and act as you would expect it to… I’ve been using mesh deform, which is giving me OK results, but not what I want. I tried the tension script, but apparently it doesn’t work with cloth simulations… I’ve considered using shape keys, but I’d really prefer to use simulation for this, as the movements may be a bit more complex. Rigging may work if necessary, but definitely not optimal. So is there any way to get this cloth sim to be more realistic?
Question #2
So I also need to have a pillow in the scene obviously, and I’d like to find some way for the pillow to interact with the main character’s head, so that he can lay his head down, and the pillow will allow for that. One method I could use is to have the boy be a dynamic weight brush, and the pillow be the canvas… Which may actually work, but I’d like to do it with simulation if possible.
Thanks in advance, and here’s a picture of an icosphere stealing the kid’s bed.