Yes to all three questions 
In my one-shot Dino Orphan, Rip is shown at a young age, and what he was like then. It also follows his mother Dawn from childhood to adulthood as well.
In the main comic, I intend on putting Rip and Freya through some traumatic situations. Rip's already been through one. It will only get more and more difficult as the story continues. The characters will indeed age physically as well while the story continues. As for timeskips there, if I do them they'll be very small.
And then we come to the alternate universes...
Any of them I create for RP purposes and even just for fun, I consider canon, in a way. (Hence why I never use characters from the comic, instead I use alternate versions.) So I've got AUs where Rip is old. I've got them where he's young. I've got them where he's dead.