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This is the first episode that I think I have a substantial criticism to so far in this rewatch, even if I did enjoy it.
The set up is strong enough, and while it took them awhile to introduce Gilda I don't think that was them meandering like I have felt sometimes in later episodes (or maybe I am just biased). Really did enjoy them setting up Rainbow Dash's and Pinkie's friendship here and it felt like a good character building moment. Gilda too, she is a alright character, I liked her slightly more than I recalled. I found her line:
Now make like a bee and buzz off!
Child appropriately cruel and mean spirited in a good way.
To my slight surprise, I take issue with this episode's moral. Pinkie Pie, Rainbow Dash, and Gilda all work as characters but the moral lesson feels a little lacking. How do I put this? Either Pinkie Pie should've been wrong about Gilda being a mean (or have partly misjudged her) OR the point of view should've been on Rainbow Dash and have Rainbow Dash herself casting off Pinkie Pie because Pinkie Pie is "uncool." That second idea feels like a episode that would apply widely to kids and would be a great lesson. I am not sure how bad I would describe this lesson. Perhaps Gilda is unfairly antagonized. What drove her over the edge wasn't Rainbow's friends so much as all those pranks and feeling targeted, even with her previous behavior (even if it was supposedly random, and some of it was). It is good to show a tough cool person not being a push over to peer pressure when it comes to dealing with a jerk and I think you could still work with that, but it feels like it needs some smoothing over. Not that I think was/is going to be a major bad influence on kids or anything.
I am split on how I feel and this split feeling carries over to my rating. Honestly, I still enjoyed this episode, and I am not the type of person to really care that much on a bad lesson or two like how I recall some would back in the day. 6.5/10 is my rating for the episode, at least provisionally. Lesson wise, this episode is a 5/10.
Odds and ends:
Stupid things that I notice and pay attention to. Twilight Sparkle used her muzzle to turn the page of a book in the opening shot with Pinkie Pie but later in Golden Oaks, uses magic.
Ponies having limited interactions with outside of Equestria races shows up here. From Rarity's "oh there quite rare". To Pinkie's remarks on having never met a Griffon. Wonder if this is more of a Ponyville or Equestria in general thing (and a context that probably changed as the seasons progressed).
I love Celestia being a second hand victim to Rainbow and Pinkie's Spike prank. Felt like a smart way to include her.