I liked a few things about this episode. For the most part, I thought the dialogue was really good. Ash's strategy to get back Oshawatt's shell (yes, finally learned its name) was a typical one from him. And then, it sort of wasn't. What I really liked, though, was how Iris taunted Ash after the victory, saying he made things harder than he needed to. I think it's interesting because it's the 3rd time that comes to my mind where a scene like this has happened at the first gym; there was also Misty's offering to Ash to use her water pokemon back against Brock, and then there was also Dawn advising Ash to use some of the water pokemon he had back with Oak in the gym battle against Roark. Iris makes her comments after Ash has won, so that makes this scene a little different. And honestly, she's right in a way. There's really no reason Ash had to make things harder here; he's got nothing to prove, and so the act seems like he's showing off. But he does back it up, and from a positive standpoint, that's a way to create respect for Ash, at least for new viewers.
However, the negative way to look at this is, again, it seems like Ash is showing off. Or, one could argue that he's Ash, and so he's doing this for the fun of the challenge. Still, I find that a bit shallow, and for old time viewers, I don't feel any better about Ash that he actually came through here. Truthfully, it just feels like a gimmick to tie in with the games (or maybe, the games had the gimmick to tie in with the anime...who knows?), and the fact that Iris emphasizes it (though I did enjoy the teasing; it was my favorite part) just makes me feel like the writers really wanted me to be impressed by the feat. And since I'm not, I feel like I'm really out of touch with what's going on.
The writers also shoot themselves in the foot in showing how impressed Cilan is with Ash overcoming a type disadvantage; seemingly, Cilan isn't very experienced, if as a gym leader he hasn't come across a challenger who hasn't won with a type disadvantage. In fact, didn't Pikachu lose with a type advantage earlier in this gym match (hope I'm remembering right)? That's really not anything to be impressed about.
On the positive side, I can see why Cilan took a liking to the way Ash and Iris interacted, and why he would want to travel with them. If this had been his sole reason for traveling with Ash, then I think that would have been more effective and reasonable than Cilan wanting to travel with Ash to learn from him. I did like how Cilan made a small joke at the end of the episode that he's traveling with Ash b/c Ash didn't answer his questions.
The professor lady was an extreme negative in this episode, to me. She seemed so shallow, and her effectiveness entirely relied on her looks, in my opinion.
I want to talk a bit more about Oshawatt, and what I meant by Ash maybe acting a little out of character. In general, I've had 2 dislikes about Oshwatt: 1 has been how much attention has been focused on it at the expense of Ash's other pokemon (besides Pikachu, which is unfortunate, in my opinon; Pikachu is an established character and doesn't need that type of attention), and 2) is how amazing its shell is shown to be. I don't really understand how its shell can be THAT much stronger than another shell. To understand my dislike for the emphasis on this weapon for Oshwatt, one scene from DBZ I took to heart was the one where Trunks fought King Cold, who proposed that the only reason Trunks beat Frieza was his sword. Trunks played along and gave King Cold his sword, and, when King Cold attacked him with the sword, easily stopped the assault, saying the weapon doesn't make the man (dubbing thing, I'm sure, but said really well). I would have preferred to see Ash win the battle by having Oshawatt use some tactic that didn't involve its shell, so that I would have a better feeling about its skills in battle (and not how amazing its shell is).