I noticed something interesting about "Letter Update" the second time I read it: the unusual forms of 'a' and 'g'.

Fig. 1: "Letter Update" with 'a' and 'g' highlighted (click to enlarge)

There are two forms of lowercase 'g': the opentail form and the looptail form. The opentail form is used in most sans-serif fonts (such as Helvetica and Arial) and italic serif fonts, while the looptail form is more common in upright serif fonts (such as Times New Roman) but appears in Droid Sans.

Fig. 2: Forms of 'g' in DejaVu Sans and Droid Sans

Looptail 'g' has two bowls (enclosed areas) connected at a "neck" (or "link") and an "ear" protruding from the top or top-right of the top bowl.

Fig. 3: Ear and neck in 'g' in Droid Sans

By far, most handwriting uses opentail g, but "Letter Update" appears to simulate looptail g. In some places it comes close, but by about the third line it sort of settles down into a form resembling a cursive 'q', but with the end of the loop raised closer to x-height.

Likewise, the letter 'a' has a 1-story form, looking like an 'o' with a short tail, seen in handwriting, in italic serif fonts, and in some geometric fonts such as Avant Garde and Lubalin Graph. It also has a 2-story form, sort of like an inverted, shrunken opentail 'g', seen in upright serif fonts, most sans-serif fonts.

Fig. 4: Forms of 'a' in Comic Sans and Droid Sans

Unlike most handwriting, "Letter Update" uses a 2-story 'a'. There's another handwritten 2-story 'a' that looks more like a handwritten numeral 2, as depicted in the Animaniacs episode "Cookies for Einstein", where "Acme" spelled backward is "Emca", or "Emc2" as Wakko Warner writes it with a 2-story 'a', inspiring Albert Einstein to state the equivalence of mass and energy.

Interestingly enough, a Waluigi Time from around the same time uses the 1-story 'a' and opentail 'g' more commonly found in handwriting. Making "Waluigi's" handwriting distinct from "Matthew's" is a subtle touch that only font geeks will notice consciously but still sets the in-character work apart from out-of-character work.

Fig. 5: Waluigi time