Rich isn't proud of a lot of the writing around female characters in the comic's early years, with particularly acknowledged low points including #35, the inn arc in No Cure for the Paladin Blues, and the general use of sexually-charged insults. Haley even delivers some Self-Deprecation on it at one point in Utterly Dwarfed.
Though he likes Elan plenty, Burlew has little fondness for Elan's initial look. This is why, while every member of the Order has seen some outfit changes, Elan is the only member of the Order to be completely redesigned, with the old outfit only being worn by him again in flashbacks and a brief gag in Blood Runs in the Family (where Haley grumbles about it).
Creator's Favorite: Burlew has mentioned in a Patreon Q&A that he doesn't actually have a personal "favorite" character to write in the strip, and instead whatever character is his favorite is whichever one he's focusing on at the moment. That all being said, he has also stated that the most fun he has had writing a specific character for a long time in the strip was actually Zhou Bo from Good Deeds Gone Unpunished due to finding her both hilarious and appreciating her character arc and related conclusion.
Demand Overload: The site used to slow to a halt whenever a new comic was posted, though this was mostly because of all the people hitting the forums.
Eugene being disappointed in Roy for not becoming a wizard is funny knowing that Roy initially was intended to be the party's wizard and the resident smart guy. Rich Burlew decided he didn't want to have Roy pulling double duty as The Smart Guy and the Only Sane Man, so Vaarsuvius became the know-it-all while Roy was retooled into a fighter.
According to the commentary of No Cure for the Paladin Blues, Roy was initially going to put on the Girdle of Masculinity/Femininity and engage in "girl talk" with Miko so he could learn more about her. While that never happened, Haley later mocks a gender-bent Roy by wondering if he was trying to use the belt to impress Miko.
Many, including Miko (not) becoming a Blackguard or Death Knight.
In the Tinkertown magic item shop, there's a bin selling "partially charged wands", a nod to an (extremely) long-running argument on the Order of the Stick forums over whether such wands can normally be found for sale.
Memorial Character: Veldrina's bodyguard Wrecan is named in tribute to a late member of the comic's forum, who would tally up character's appearances.
No Origin Stories Allowed: The author has stated that he's never going to give an origin story for Belkar because doing so would risk making his behavior be less funny and more sympathetic. The closest thing he's gotten is "Uncivil Servant", a short story that explains how he became an adventurer, but which depicts him as basically fully-formed with no real differences in personality to his modern counterpart.
Official Fan-Submitted Content: The characters Veldrina and Wrecan. In the Kickstarter campaign, one of the prizes for large backers would be to have their character have a walk-on cameo for a single page, though the character fit perfectly for a then-upcoming arc in the story, so Rich opted to keep the character for longer. Wrecan is included on a more somber note. He was a prolific poster before suffering from heart failure. His wife said he would have loved to have been included in the comic, so Rich included him.
Wrecan's remark about counting the appearances of legacy bearers is a reference to how the real life Wrecan started the "number of appearances per character" thread.
Their words of farewell to each other, with the "camera" angle facing Wrecan head-on for the second half, as if he's addressing the reader:
Roy: I'm...I wish there had been more time. To get to know you better. Wrecan: There's never enough time. Every day, one after another, until we wake up and it turns out that's the day our world ends. You have to do what you can, when you can — because who knows if tomorrow is even happening, you know?
The strip is titled "Mark of Distinction" as a reference to his real name, Mark Monack.
Schedule Slip: Early in the comic's run, the author kept up a fairly regular Monday-Wednesday-Friday schedule. Health issues eventually made this impossible to keep up on a regular basis, and he experimented with other schedules before finally giving up and making the official schedule "Updates at random". By the time this happened he was already one of the biggest names in webcomics and his site received more traffic than Marvel's, so it hasn't hurt his fanbase.
Science Marches On: This strip has a gag that a Brontosaurus being just an Apatosaurus with the head of another dinosaur is no reason for it not to exist in a world with griffons and chimaera. The problem is, this is being reconsidered after a 2015 study that concluded it's a different genus after all (although the original head is still wrong).
Series Hiatus: Starting September 2012, the comic was in an enforced hiatus after Burlew seriously injured his drawing hand in an accident. Updates didn't resume until the end of 2012.
According to a Patreon Q&A, Azure City being colored blue along with virtually all of its citizens having naturally blue hair came as consequence of Burlew needing to clearly distinguish the characters' arms and mouths from their hair (i.e., O-Chul's beard is blue instead of black so that his mouth is visible). He learned this problem while drawing Miko, whose long black hair meant that her arms had a habit of vanishing when she raised them.
In the intro to Utterly Dwarfed, Rich explains that many decisions made in the plotting were in some ways affected by the artstyle. In War and XPs, the stick limbs had a habit of melding together with each other, which led to Don't Split the Party having fewer scenes involving large groups of characters. The problem was somewhat alleviated in Blood Runs in the Family by the hazy, dusty desert setting allowing for fade effects on background characters. Utterly Dwarfed was the book that forced the switch to the comic's current artstyle, due to the sheer number of scenes taking place onboard the Mechane, which meant lots of scenes with complicated backgrounds that risked the character's arms and legs overlapping with background elements.
Shrug of God: While The Giant is fairly forthcoming about things most of the time, some questions are met with this so he doesn't close off avenues for future plot. He's refused to state — or even decide on — the Order's actual levels, for instance, and when asked if the three souls spliced to V during Don't Split The Party were from previous versions of the world on Patreon, he responded that it's a reasonable explanation, but he didn't want to nail it down in case it somehow becomes plot important that they aren't.
The idea of Durkon turning into a vampire came up early to Rich Burlew, when the comic was still a gag strip with no continuity, to make a Pun on "Turn Undead". Then the author decided he wanted a more continuous storyline, and the concept evolved into a lengthy story arc which saw Durkon killed and raised as the High Priest of Hel.
Miko was originally going to be introduced fairly early, and be a much softer character, with Roy's unrequited crush being the focus of her character. Rich reworked her heavily when she did show up, and though the Ship Tease did crop up in her early appearances, it was swiftly abandoned due to Rich finding the two didn't have any chemistry. Additionally, though her ultimate fate was already planned out by the time of her first appearance, it was at one point going to occur later in the story, which sparked a lot of confusion thanks to a note at the time that suggested she'd be sticking around for much longer than she did.
Word of Gay: In outside material (such as the retail version of Blood Runs in the Family and his Patreon), Rich Burlew confirms that Vaarsuvius is genderqueer. However, he states they don't explicitly identify that way due to elven gender expression and identity being different from that of human gender expression and identity.
[Vaarsuvius] would have no reason to adopt the term as a stated identity. And if V wouldn’t use the word, no one else is in a position to put that identity on them. Except me, I can say whatever I want about V because I made them.
Burlew has also confirmed in the author's commentary for Utterly Dwarfed following some Ambiguously Bi hints in previous volumes that Haley is bisexual, and is only "straight-passing" through her current relationship with Elan.
Write Who You Know: According to the February Patreon Answer Post, Durkon's uncle Thirden was based off the bard character of one of Rich Burlew's high school friends, but only in name, appearance and broad personality. His backstory and relations with Sigdi are Rich Burlew's own creation.
Roy's skin tone was lightened a few shades after the art upgrade. Word of the Giant says it's so he'll appear better when the books are printed. The same thing happened with Zz'dtri.
Elan's costume upgrade in War and XPs is a reference to Locke's outfit from Final Fantasy VI, minus the wig and bandanna. After escaping from prison, he dressed up as Locke (and Thog donned a Moogle suit) to sneak aboard the Blackjack, then gave himself away, got thrown out of the airship, and never changed back. The new costume's a large improvement, though.
As of his resurrection in #665, poor old Roy had been dead for exactly one third of the comic.
The following titles have each been used for two strips: "All in the Family", "The Bright Side", "Breakfast of Champions", "Loose Ends", "A Moment of Truth", "Not to Scale", "Resource Management", "Role Reversal", "Running on Empty".
Rich Burlew is known to sometimes indulge in Exact Words in the forums as not to spoil some yet unrevealed twist in the story. For example, when pressed about what god Vampire Durkon would worship after his death, Rich pointed out that non-theistic clerics can exist in D&D, and that it was likely for a cleric turned vampire to become one. But he never specifically said that Durkon was such.