I think for me it's mostly linked to a combination of seeing far fewer latter era episodes and the growing feeling that any episode that felt like it had meaningful growth would just be overwritten next series anyway.Well it’s inevitable with so little Krazyshipping in latter days eh?
I absolutely adore how Sabrina is portrayed in the OS. A true badass. The "creepy girl with supernatural powers" aesthetic just makes her more appealing to me. This is my favorite iteration of Sabrina overall. I thought the section where the gang is shrunken down and stuck in a dollhouse was awesomely dark. I also love how there are humans with psychic powers in the Pokémon universe. Really helps flesh out the world and makes it more interesting than just "the real world but animals are replaced with elemental monsters." It also leads to awesome fan theories and adds a bit of mystery/intrigue. Psychic is one of my favorite types, too.
Hoo boy. I used to be absolutely obsessed with this episode as an edgy middle schooler. Watched it over and over again on YouTube. Remember AMVs? Yeah, I watched a bunch of those featuring Evil!Ash / the King of Pokélantis back then too. I guess I still haven't grown out of my "good guys turned evil" phase seeing as I'm placing it high on this list. I just love that trope, OK? Evil!Ash / the King of Pokélantis is one of my favorite Pokémon anime villains for his creative ruthlessness like when he ordered Sceptile to hide behind the referee. I even give him points for going after Ho-Oh, one of my favorite legendaries. It's a shame that he doesn't return at any point in later seasons of the anime. Would've made for some nice conflict (from... within eh eh?). Finally, I enjoyed the scenes with Team Rocket and Brandon's big "NO" as always.
This is just a filler ep but it's so fun! Love Lily's English dub voice (hehe Bri'ish). She's a cute little witch with a Murkrow, what's not to love? Apparently magic exists and can turn people into Pokémon (if only temporarily)?? This is the episode that spawned "Ashachu" (Ash as a Pikachu). Definitely memorable for that reason alone. I also love the way Ash says, "In that case, this is AWESOME! I'm a Pikachu!" and later starts playing with Pikachu, Murkrow, and Togepi. The People Turned Into Pokémon thing might've been transferred to my love of Pokémon Mystery Dungeon.
The OG "Ash cross-dresses" episode. Sets the stage for all future Ash cross-dressing episodes that happen every generation (afaik, idk about Journeys). It's one of the most consistent things about the anime, honestly. Gives me an odd sense of comfort whenever I hear one of these types of episodes has come out ¯\_ (ツ) _/¯ Oh and the reason I chose this episode rather than any of the others is because this Ashley is my favorite. He surprisingly pulls off the blond look.
This and the rest of the episodes from the DP Pokémon Summer Academy arc make for a fun excursion on the side. Some of my favorite things: Loved Ash and Angie's chemistry I ship them tbh, especially when they got in trouble with the teacher and were held up by their collars like a pair of kittens; We get to see more of Professor Rowan - he's underrated imo; Every scene with Conway in it (I go wild whenever he's on screen); Raichu being adorable; Team Rocket (especially James) were excellent as per usual. Another memorable thing was when screenshots of Ash with his borrowed Raichu were revealed prior to the episode airing, people went crazy thinking Ash's Pikachu had evolved finally.
Your first two entries scream edgy lolHere is my list of top 5 favorite episodes. These aren't necessarily my most replayed episodes - more so ones that left a certain impression on me:
Abra and the Psychic Showdown
Battling the Enemy Within
Camping It Up!
Some honorable mentions I won't go into too much detail with: Pokémon-I Choose You! (the one that started it all); Charmander-The Stray Pokémon (heartrending); Here Comes the Squirtle Squad (Squirtle Squad ftw); Pikachu's Goodbye (all of the tears); Bye Bye Butterfree (yet more tears); Bulbasaur's Mysterious Garden (magical); Holy Matrimony! (James-centric goodness); Go West Young Meowth (Meowth's backstory); The Ghost of Maiden's Peak (bizarre, in a good way); Gaining Groudon (Pikachu gets possessed); Malice in Wonderland (a trip from start to finish); Pika and Goliath! (has my most watched battle, nice homage to the first Pikachu vs Raichu battle); A Crasher Course in Power! (favorite gym battle); Top-Down Training (Cynthia and her Garchomp are awesome)