The Results

Sorry for taking so long. I was hoping for slightly more participation!

First View:

Memaw Said, "Maybe a Dinosaur."
Jack Said, "A Smily Face"
Granpa said (in person), "A Dragon Eating a Chicken"

Second View:

Memaw said, "Maybe Memaw trying to hug a little boy?"
Jack Said, "Some kind of forest."
Granpa said (in person), "A Dragon Eating a Chicken"

Third View:

Memaw Said, "Maybe Socks the cat?"
Jack said, "An Entrance to a cave."
Granpa said (in person), "A Dragon Eating a Chicken"

Fourth View:

Memaw said, "I just do not know, you will have to tell us what Trevor thinks it is."
Jack said, "Upsidedown!"
Granpa said (in person), "A Dragon Eating a Chicken"

And the winners are:
Memaw for the greatest number of question marks!
Jack for seeing the forest for its trees!
Granpa for actually coming to close to what Trevor says it is...

A DRAGON! (The two circle-ish things in the first view on the left-ish side of the page are its eyes.)

Interestingly enough, I thought it was a chicken.