Using the power of Google and overthinking, the characters' names have been investigated.
Will gained his last name because he helped make the treaty with the Skandians, so that's obvious. But Halt and Will's names are technically words as well. People have willpower, a will to do good (or evil), including Will himself, and he's proved it time and time again. Halt's name also suits him. He puts a stop to evil, often by shooting the issue before it becomes a bigger one.
Horace can mean timekeeper or be a version of Horatius, a Roman jester. The first meaning makes sense with his steadiness and reliability.
I didn't like what I saw in the Urban Dictionary for Gilan and have not gone back to investigate what I read.
Alyss has a German origin and means noble, which she certainly is. However, Pauline definitely isn't small in any way. Arald has many meanings, a few of them about being heroic and kind. Cassandra has ties to Ancient Greek, where she had prophecies but no one believed her. George means farmer, and Jenny means many things, one of them being fair.
Duncan seems to stand for dark/brown warrior. It's possible the name was inspired by Macbeth, since I once found similarities between the play and the Ranger's Apprentice books. Apparently, there is an Oswald in King Lear.
Crowley's name is really funny because in recent media, two other better known Crowley demons exist: one in Supernatural, and one in Good Omens. The former is inspired by the book form of the latter, though the TV form of Good Omens changes Crowley in ways like making him a redhead, like the Ranger's Apprentice version. The name Crowley may come from an old occultist.
Crowley has a more subtle alias by the name of William Morris, which is the name of a talent agency representing actors, or a guy from the Art Nouveau movement, or a British writer known for medievalism. Also, in an original Sherlock Holmes case, a cheerful, short, redheaded guy is introduced as Duncan Ross—an alias, where his real name is Archie. This redhead had a secondary alias too: William Morris. I'm not sure which of these is inspiration, if any, but it's funny that most of them fit.
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