Names, Names, Names

It's in my nature to geek out over names. I love names and knowing what they mean, and when I give the names to characters, I really like it when the names mean things for the character.

I recently started outlining a story that I've been kicking around for a while, and I noticed a slight flaw with the names. A pattern had formed with the naming that I liked: the upper class had English names, the middle class (largely absent from the text but occasionally present) have French names, and the lower class (mainly the thief's underworld) have Italian names. There are just two spots that are niggling me.

~Leo: The prince (a major player in the book) and also the chief of police. The appropriate English name would be Leonard. Now, I've probably got some sort of implicit bias in my mind, but I don't really like that name. I don't like the sound and much prefer the Italian Leonardo. My concern would be is it worth compromising the structure that I had previously developed with the other names. My rationalization function tells me that he will go by Leo for most of the book, so I can skim over that detail. Also, since he'd be spending a lot of time with the members of the underworld, he could get away with an Italian name. My persnickety side does not really like my rationalizations but isn't sure how to change the name well, because I want to keep the nickname Leo.

~Maggie: She's a comparatively minor character (medium sized role) but a thief. In theory, she should have an Italian name. The closest I could swing a name like Maggie is that it might be short for Marguerite, which is French, but the nickname Maggie is shamelessly English. A similar problem faces me with this name, since I'm not sure how much I want to move outside the system I'd already established and how much I can expect a reader to overlook. On the other hand, I'm much more flexible with this name.

Any advice (or commiseration) at all would be much appreciated.