Parker Luck and "Relatability"

[Huntsman Spider]

Peter cares about money in the way most people care about money: because he doesn't have enough.

Yeah, that about sums it up.

[Mister Mets]

If you want Spider-Man to be a superhero who typically has his shit together, I don't think you understand the series.

There is potentially a take on Spider-Man as a hero who used to struggle more, but now has a better work-life balance, although I'm not sure that works as well as a story engine. It doesn't seem like a perspective that results in decades of new stories.

[Daibhidh]

If you want Spider-Man to be a superhero who typically has his shit together, I don't think you understand the series.

I think that's flanderisation. Peter mostly has his shit together in the Ditko/Romita eras or the Stern/DeFalco eras - sometimes it falls apart in a big way but mostly it's together. The point is though that Spider-man is a lot of extra shit to keep together, or depending on your perspective Peter's civilian life is a lot of extra shit to keep together, and so Peter has to work a lot harder to keep his shit together than most heroes do.
Peter doesn't lose to his villains all the time. It looks like he's going to lose to the villains but then he comes up with a clever plan and saves the day. In the same way, Peter doesn't lose his shit all the time. It looks like he may lose his shit but then he finds a way to pull it all back together again. (I'd argue that instances of his really not keeping his shit together in earlier eras are actually examples of him looking like he's lost it completely but then finding a way to pull it back together against the apparent odds.)
So Peter catches the flu and in a fever he decides to reveal his identity to all his friends. (In the logic of the comic this is a bad thing.) He's lost all his shit. But then because he's earlier made friends with Hobie Brown instead of just sending Brown to prison, he's able to convince everyone he's not Spider-man and he gets everything back the way it should be (according to comic logic).
In Straczynski's AMS 49, it looks like because of a basic romcom error and an unfortunate coincidence and Peter forgetting to pay his phone bill, Peter and MJ's marriage is finally over. If you stop reading the issue two thirds of the way through it looks like Peter has really not got his shit together. But then through another heavily foreshadowed coincidence they get another chance and it all works out.
Peter only doesn't have his shit together if you stop the story before the climax.

(The deaths of Captain and Gwen Stacy were powerful because they were anomalies then. They should still be anomalies now. Nobody cared that they killed off Flash at the end of Slott's run or cared in the way intended that they killed off Kamala Khan because everyone knew the deaths wouldn't stick.)