I agree with your comment about the casting. Winn is more of a Jimmy than Jimmy is. Why not just switch them around?
(I am trying to put aside my frustration at the fact that all of the comic book redheads are the ones who are being race-swapped. Jimmy Olsen has never been played by a redhead, despite being a redhead in the comics. Yet, everyone is saying how great it is to see a different take on the character. I'm not offended, necessarily. I've just been paying attention to the redheads that I do see on TV lately, and I've noticed that they're usually bullies or bad guys. Not cool)
Ultimately, the problem with Supergirl is that the whole premise of the show is that she isn't Superman. The audience is constantly left to wonder why he isn't there. Why is she fighting his villains. Why is she living his life? The show is pretty much just gender-swapping Superman most of the time. And it's a shame, because Supergirl has a story that Superman can't tell. He is essentially human, she is not. He can't really feel the pain of losing his home the way that she can. He can't really feel like an outsider the way that she can. But rather than play up the uniquely Supergirl stories, they just keep making her not-Superman.
She shouldn't be working for a news outlet. Jimmy shouldn't be there. Lucy Lane and General Lane shouldn't be there. Maxwell Lord is just not-Lex Luthor. Astra is just not-Zod. And they keep giving Supergirl Clark's enemies from the start, like Livewire and Bizarro, so... who has Superman actually fought in this universe?
Now, they are going to bring in The Flash. Barry Allen will meet Supergirl before Superman. They will undoubtedly do the race that we usually see between The Flash and Superman. It's all just wrong.
It's like they didn't actually want to do a Supergirl series, but they couldn't get the rights to Superman, so they were stuck with her. Now they have no idea what to do with her, so they just make her not-Superman. I don't feel like they have the same level of excitement about making this show that we see with The Flash or Legends of Tomorrow. It's so sloppy that they regularly have characters shouting huge secret information in the middle of crowded rooms.
I find the show extra frustrating, because it didn't have to be bad. But it is.
Speaking of Curtis... if he is supposed to be an Olympic level athlete, why did they cast someone who is rather physically unremarkable? This is someone who would have been training hard, for way longer than Oliver has been. So, I would have expected more.
That aside, my complaint about Supergirl's writers being bored and lacking energy goes for Arrow as well. Felicity's paralysis storyline wasn't even played up as much as Barry's was, after his Zoom attack. We knew that he wasn't going to stay in the wheelchair after that, but it was still played more dramatically than Felicity's story. Now they have her acting as though she's been this way for years, without a single setback or moment of frustration (much less, months of therapy). They have her sitting in her wheelchair UPSTAIRS at their apartment! And now they've introduced the McGuffin to make it all go away. So the question is, why did they bother? It's like lighting a character on fire and having them just sit there, watching TV, never stopping to notice or care that he is on fire.
I don't understand why Malcolm is sitting at the evil dinner table of doom with Damien's evil sidekicks and hands over Oliver's son, yet doesn't just tell Damien who Green Arrow, Black Canary, Spartan, Overwatch, Speedy, and for that matter, The Flash are, under the masks.
None of the motivation makes sense on the show anymore, and it feels like the writers don't even care about that. These are obvious issues that the writers could easily fix, but they don't.
And why is Oliver willing to bend over backward to stay friendly with the woman who stole his kid from him? I don't get it!
The Flash --
I'm not sure who the man in the mask is. I've seen theories that it could be Earth-2 Wally West, but I don't know. Could there be more than two Jay Garricks? Or could the Jay we know not even be Jay at all (his double is named Hunter Zolomon, after all).
What does everyone here think of Wally West so far? I've been a fan of his in the comics for years, but I'm not really liking this version of him. He comes across as very whiny and selfish, and there is no extra charisma or chemistry with the rest of the cast that makes him anything more than that.