Well... at least it's not season 4?
Okay, that's not entirely fair. Compared to season 4, season 5 is on one hand much more ambitious, but on the other hand far less consistent. It's not a stale chore like the previous season, and its high points are significantly higher, but its low points are significantly more frequent. Characterization is still not consistently good, which is disappointing after five seasons, and the number of episodes which fall entirely flat is significantly higher than the norm. In spite of the raised ambitions of the season at large, the vast majority of it is still overwhelmed by a feeling of stagnation, as the breaks from formula are usually quite mild, and very few meaningful changes are made to the status quo. The most frustrating thing about it is, perhaps, that the main six don't really get much more development than they do in season 4, to the extent that attention is rarely placed squarely on them in a truly meaningful fashion.
That might actually be by design, as a large aspect of this season is focus on secondary characters. Several episodes have their primary focus on a secondary character, many of whom are likely to never have another major appearance. I mean, really, does anyone actually expect Trouble Shoes to make another appearance? Surely not. And yet, a number of these secondary characters have proven popular, most notably Coloratura and Moondancer. But even if these characters do appear again, it will be a special occasion. Exactly two of the episodes not centred around one of the mane six or Cutie Mark Crusaders are actually focused on returning characters, which might have been easier to appreciate if at least one of the mane six weren't in each and every one of them, gaining absolutely nothing from the experience. It makes the occasion where character development actually occurs an especially pleasant surprise, but it also makes the season really frustrating.
With all these characters, there's a unifying theme of finding the best in everyone. Everyone is better through friendship, and that is shown repeatedly through the season. While the details and the primary theme might change from episode to episode, the sheer number of episodes about making some random character better through the magic of friendship renders the season a little formulaic, particularly because the majority of the episodes which don't fall under that umbrella are somehow even more standard and formulaic. While the Cutie Mark Crusaders get considerable character progression, to the point of being involved in the season's biggest plot event, the mane six are, again, largely stuck in place. Episodes like "Canterlot Boutique," which are clearly geared towards moving a character forward, are downright revelatory when they should be commonplace and expected.
Tonally, season 5 is remarkable for actively going darker than My Little Pony ever has before. This is most evident in the opener, with its distressingly realistic depiction of a cult, but it also appears prominently in the finale's potential bad futures. Particularly in its earlier episodes, though, this season has been weird. Perhaps this is due to coming after the aggressively safe season 4, but much of season 5 is filled with unexpected choices which make the season just a little more idiosyncratic, if still irritatingly stagnant. Episodes like "Party Pooped" are wholly bizarre, whereas many others merely contain the occasional idiosyncrasy which stands out amidst the usual formulas. It's something, I guess, and in a show which is increasingly stale, it's in need of a little something to keep it just a little fresh.
Of note is just how poorly the season takes advantage of Twilight's new status as a princess. Only the aforementioned "Party Pooped" has her acting like an actual princess, with the majority of the season having her (and her friends) going on "friendship missions" to spread friendship to places in need of them. The whole idea is uncomfortable, and worse still, it's mandated by a plot device which is somehow even lazier than the box from season 4. Where the box was at least interesting and mysterious, in spite of being largely ignored, season 5's map is a transparent excuse for certain characters to go to certain places and do certain things that the show clearly expects to be taken at face value. It goes by unquestioned, and only gets more insufferable each time it appears. Each episode with the map might as well be self-contained, as there's no real flowing narrative to the season.
What makes season 5 so frustrating, however, is that it frequently does show inspiration. There's plenty of good ideas scattered throughout the season, but many of them aren't developed beyond the episode they first appear in. Episodes like "Bloom and Gloom" and "Crusaders of the Lost Mark" demonstrate that the show can be affecting while still moving its characters forward, and even episodes like "Amending Fences" try to go for something much deeper than the usual. However, there's no real focus, and as a result, the season as a whole frequently feels directionless. Perhaps season 5 is the writers trying to figure out what works, but rarely does it quite reach the level of craziness that would imply, and there's numerous irritatingly conservative episodes which have little to say about which direction the show should go in. The stretch of episodes from "Canterlot Boutique" through "Crusaders of the Lost Mark" in particular is packed with ideas that made it really look like the show was picking up its pace, but it was immediately followed by an expansive string of episodes that add subtle, minute things to the show which fail to balance out the increasing sense of tedium from a season which continues to play it safe.
Five new writers were added this time around: Nick Confalone, Neal Dusedau, G.M. Berrow, and the duo of Joanna Lewis & Kristine Songco. The latter pair got off to a rough start and frequently struggles to provide a truly compelling main plot, but "Castle Sweet Castle" aside, they're very good at making clever, thoroughly entertaining episodes, and more than most other writers they seem to have a real vested interest in the main characters' growth. The superb "Rarity Investigates!" has its brilliant cold open, but "The Hooffields & the McColts" also demonstrates that, in spite of some issues, they are interested in what makes the protagonists tick. Confalone has issues with tying his stories together, managing to make "Party Pooped" cohere mainly through blasting it over-the-top, and ultimately struggling to do the same with the more subdued "Hearthbreakers," but he also has perhaps some of the most intriguing ideas out of any writer on this show. "Party Pooped" explores the stresses of being a new, untrained princess, while "Hearthbreakers" takes a look at how two very different families can bond over shared experiences. If he can figure out how to make more cohesive, subdued scripts, he might be able to become one of the best writers the show has ever had.
It's hard to say as much for Dusedau, who has thus far demonstrated a small capacity for decent jokes but a large inability to properly write characterization or pace his episodes. Both of his episodes to date are almost unanimously agreed to be of low quality, and unfortunately there's no real glimmers of hope that his next will be any better. Berrow has only one episode, and unfortunately it's "The One Where Pinkie Pie Knows," a void of an episode which lives or dies based on how entertaining you find its one note joke to be. I didn't find it all that amusing, and while I haven't read her previous work with the franchise (she is the writer of the My Little Pony chapter books), her one episode is not a great representation of her abilities.
It really might have been something, y'know? In its fifth season, My Little Pony seems so close to finding the right balance between remaining kid-friendly and growing up. But every other time it tries, it only calls more attention to its deficiencies. While a better array of episodes would certainly make for a better season, what's truly missing here isn't merely a majority of quality episodes but a consistent feeling of progression. It's the inconsistency of that progression, which only appears in spurts, that renders season 5 far less tedious than season 4, but still deeply frustrating. The show can be so much more than it is, and it doesn't even need to be everything it possibly could be, but it'll continue to be a shadow of its potential unless it can increase the character development and have more events of consequence. Season 5 is a start, but it's not yet where it should be.