Of the DND-based entries in the jam, this is definitely the one that captures the game best - both in the specifics of play, and in spirit. Everyone here has two facets to them - the player, and the character - and both affect each other equally. Disagreements arise between players, or between them and the DM, and gathering everyone for every session is impossible, but when I look at the DND sections in the story, I find myself convinced that these characters really are a party, and that they do enjoy this in some form.
Of course, it's a shame for them that the surroundings are... less than ideal (in a way that makes for a very entertaining read). You can practically feel the awkwardness in the setup itself - Tyler being the 'creator' of the campaign, but being within the position of a player - which, to me at least, reads as him being so caught up in his own depression that he unintentionally makes Greg "pick up the slack" an play the role of the DM in his place out of sheer inertia. It's something that the story does very well - it showcases both the severity of Tyler's own depression, and how that depression can legitimately hurt his friends in turn - which only serves to feed it further, in a warped way.
Which isn't to say that Tyler's at fault here - or that anyone is, really. I think that the characters here are written very well - they're realistic in their behaviors, and even the more "antagonistic" ones still do so in a way that's ultimately believable for a friend group. At the end of the day, Tyler's perspective is a very limited one, due to his own tendency for metaphorical self-flagellation, and his firm belief that there's nothing that can be done about the poor circumstances of his life. After all, the butterfly has already flapped its wings - what more can he even do now?
With all that praise said, one thing that I do think is worth noting is that the story was slightly hard to follow - part of me thinks this might be intentional, given how depression can often make days meld together in a dream-like way, but with the bulk of the story being in the sessions, and with us not being able to really tell what occurs in between them, I'd frequently get confused when characters would refer to things that happened off-screen and I'd have to pick up the pieces myself. It might be intentional, but given that Tyler is presumably well-aware of these things himself, it felt like it made the reading experience a bit harder than it should have been.
As for the presentation... there really is so much good here - Sikyu's backgrounds are absolutely incredible and capture the fantasy world with a sense of vividness that really helps pull you into the DND, and the custom sprites are also really charming. What's most impressive to me, though, is how well everything is combined - custom sprites, premade sprites, photo backgrounds, painted backgrounds - all of these disparate parts are brought together in a way that feels like it fits really well, in spite of the conflicting art styles. I'd say Maybe Josh's sprite felt a bit out of place given the thick lineart, but that's just how the premade sprites go, and I think you did a fantastic job with putting it all together regardless.
If I hadn't made it clear, I think this was a really great entry to the jam, and I'd wholeheartedly recommend checking it out.