1. "like fallen leaves" on its own makes me think of something dead - picturesquely dead but dead nonetheless. So I think it would depend on the context - if the character in question was clearly alive, I would be more likely to think "dying", or even more towards "dry and cracked".

2. I think I would only get the names confused if there few facts to distinguish the characters from each other. Not if one or both were a main character. I would like to say, "No, of course not," but I remember reading a chapter of something (The Iliad, I think) out of context for uni, and it was full of characters whose names all started with A. And we all got very confused.

The first pronunciation which comes to mind is be Ay-merry (as in "a merry christmas) and Ahr-REN-yay.