Look, season 5, I'm glad you're trying, but a semi-decent idea is kinda ruined if everything around it is awful. Remember, spoilers follow.
It's been a while since I've seen My Little Pony fall so flat on its face. "Appleoosa's Most Wanted" is staggeringly terrible in nearly every aspect, only eleveated by having a somewhat decent moral-but even said moral is so ineptly delivered that it'd have to be incomprehensible to be any worse. Between a general lack of creativity and general sloppy execution, this is a definite low point for the season.
With these Cutie Mark Crusaders episodes (and yes, this is a CMC episode), they almost always begin with the Crusaders seeking their cutie marks. It's so common that it's non-indicative of the episode's quality, though most of the time the episodes where they're not seeking cutie marks are their best. This is in that category: Instead of being about the CMC searching for cutie marks, it's about the CMC helping someone else understand their cutie mark. The ultimate lesson of this is "when life gives you lemons, make lemonade", but it tries to merge that with "you are whoever you want to be" to sloppy results. In the real world, people aren't assigned a talent which they're forced to understand, and thus a story about someone understanding his butt tattoo doesn't resonate. This is driven home when the episode attempts to explain its moral not once, but twice and still has to repeat the second one right after because it keeps failing.
Season 4 didn't say much about cutie marks, but they've returned in a big way in the fifth season, with the excellent "Bloom and Gloom" finally pointing towards a conclusion to the Crusaders' cutie mark obsession. In that episode, Apple Bloom and friends worried about getting the wrong cutie mark, which worked in the context of childish worrying and actually made some sense in context, even if it followed the "cutie marks = destiny" garbage brought up by the abhorrent S3 finale. "Appleoosa's Most Wanted" doubles down on that, giving the new episode's new character a bad luck cutie mark. If any episode reinforces that cutie marks are just given to ponies and that they have no say in the matter, it's this one, which is frustrating because cutie marks started off seeming like an extension of the pony's will; a representation of their passion. This final confirmation that whatever free will ponies have is futile is particularly depressing.
Trouble Shoes, the episode's new character, is an outlaw whose crimes are the result of a bad luck cutie mark. If that sounds depressing, it's only because it is, and it makes the tone of his scenes unbearably dour. Someone who's doomed to cause ponies misery because of his bad luck is an extremely tragic premise, but as this is in service of the episode's deeply misguided moral, this tragedy amounts to far less than it could have, to the point where his crimes are so minor that he didn't even need to be an outlaw, despite the title. In a different show, this idea could actually make for a really good longer episode, but here, it doesn't amount to too much, and because of that his complaining actually gets a little annoying. Worse still, the kid-friendly nature of the show reaches pretty grating levels when a Western town's "most wanted" is someone who ruins rodeos with his clumsiness. His design's pretty good, at least.
Applejack makes a completely unnecessary appearance in the episode as a side character, and her complete lack of any respect for Apple Bloom-as seen in the abysmal "Somepony to Watch Over Me"-is on full display here. She comes under the impression that Trouble Shoes abducted the CMC based entirely on a hunch, and when the CMC try to tell her that they ran away, she just ignores them. Then again, the CMC don't seem to object too hard to that anyways for some reason. Because of this, the Crusaders have to break Trouble Shoes out of prison, and this actually gives us a solid moment where we actually see Sweetie Belle using her magic. The episode has a fair number of jokes, but just about all of them are tired and unfunny. Only the penultimate scene was anything that I haven't seen a hundred times before, and even then it wasn't THAT clever.
Even if the rest was a little better, this episode is sabotaged by some truly dreadful pacing. Scenes just come and go, moments move by so quickly that they don't really sink in, and just about everything is glossed over. This is the most rushed episode since "Magical Mystery Cure", but it's even worse than that, because at least "Magical Mystery Cure" left something of an impact, and at least it TRIED to work in spite of the short MLP episode running time, as seen in the decision to make the episode musical. "Appleoosa's Most Wanted" is just a mess.
It's really a shame, too, because this episode does show some maturation from the CMC, and has those fillies-and thus, us-coming to understand things about cutie marks. However, not only are these ideas poorly executed, but their relevance to the CMC is woefully underdeveloped, and what's left is merely filler. While other episodes have made me angry, it really has been a while since I've seen one this shockingly awful. I expected a fairly unremarkable episode, but this is just inept. Hopefully next week's better.