I like the medium size and I know what you mean about the initial "I" being tricky... it's my daughter's initial and necklaces never seem to look right with just an "I" for the initial. I've opted to go with her nickname to put on things around her room, so when I get into getting her initial jewelry - I think I'm just going to get that in a "B" (beginning of her nickname) because it's a "prettier" letter.