Warning--I start off in non-spoiler territory, but spoiler territory tends to sneak up on me. Its probably best to hold off on reading this until you've seen Spider-Man Homecoming.
This may have worked against my enjoyment of Spider-Man Homecoming. I'd like to say up front that I did enjoy the movie. This isn't like when I felt like to had to take my difficulties with Iron Man 3 to the blog the same night that I saw it, because so much of it didn't work for me. This is a matter of a good film that I wanted to like more, and me trying to figure out why I didn't.
What Worked For Me
Right off the bat, I love Tom Holland as Peter Parker. That is brilliant casting. He is energetic, enthusiastic, and he's able to be upset and kick himself without making me start to dislike him. He has realistic and entertaining interactions with the people around him.
To unfairly bring in other portrayals--Toby Maguire's Peter Parker could get especially annoying when he became morose, and Andrew Garfield's was a little too cynical and damaged to fit what I think of when I think of Pete.
The dynamic between Pete and Aunt May was certainly better than in the Andrew Garfield reboots. Sally Field's Aunt May felt angry all of the time, and especially angry at Peter, which put up some boundaries between feeling a connection between the characters.
I really loved Michael Keaton's Vulture. He brought some of the old "tough guy everyman" that I remember from the earliest roles I saw him in, and that actually made for a really interesting contrast to the "young, enthusiastic everyman" vibe that Pete had. In a way, that made for a better contrast of opposites between Vulture and Spider-Man than I thought was going to be possible. I also greatly enjoy that Vulture was still a "victim of circumstance doing the wrong thing for the right reason" that we saw in the Raimi movies, but instead of Raimi's tendency to absolve his villains their faults with mental instabilities and redemption scenes, Vulture owns the man he becomes.
With a few exceptions noted below, I enjoyed the cast of younger actors that were Pete's fellow students.
What Didn't Work For Me
There is a disparity of competency between Spider-Man as he appeared in Civil War, and Spider-Man in this movie. I don't want to get into it too much, but the Spider-Man we saw in Civil War was able to hold his own with trained Avengers and improvise tactics and adapt to the changing battlefield. In fact, there is a line that attempts to reconcile this in the movie that, if taken literally, kind of cheapens Civil War for me.
Not every Spider-Man story needs to have Norman Osborn, Harry Osborn, J. Jonah Jameson, or a reference to Uncle Ben. I didn't want a rehash of previous stories or another origin story. However, as presented, it almost feels like those things have been excised, not just avoided. "A bad thing" happened to Aunt May. In the context of the movie, Oscorp would have been very easy to reference, without invoking it's CEO or its heir apparent, but it's not there. When we see news reports of Spider-Man, we don't hear anything from the Daily Bugle, J3 communication, or anything of that nature.
I miss Spider-Man's spider sense. It was alluded to, kind of, in Civil War, as possibly just heightened senses that don't always work, and tend to overwhelm Peter when they kick in, which is why he built the goggles to adjust. There is zero reference to that in this movie. I suspect it has to do with the next thing that doesn't work for me, and having some messy storytelling to integrate both items.
I really don't like the Stark created super-suit. The suit has so many gadgets and so many enhancements that it almost feels like Tony could have just built a suit that gives someone Spider-Man's powers, at which point there was really no point in recruiting Peter. He would have found an adult pilot for his Spider-Suit. I know this was part of the pay off for how the third act played out, but we still have a "baseline" Spider-Man with a suit that obviates the need for Pete to develop some of the technology and skills he develops himself over the years.
Ned's comment lampshading the "guy in the chair" doesn't get me to forgive the movie for making Ned the "guy in the chair." Even when Spider-Man has people to confide in, his story is very much being the guy on his own when trouble starts up, and adding an a trope that is bordering on cliche into a character that didn't really have that before doesn't feel right.
I hate using names for character rope-a-dopes. I'm not saying you have to make a character exactly like they appeared in the comics, but I consider it a different thing to intentionally use a portion of the audience's knowledge of a character against them. It's cheap heat. They do it twice in this movie. Pete's got a crush on someone named Liz? Hah! Gotcha, it's not that Liz! Pete knows someone that is a misanthropic outsider and their name is Michele so you think she's not suppose to be related to any previous character? Ha! She says to call her MJ, meaning we didn't really change MJ, but we redefined what MJ actually means!
If you want to introduce characters into the story that weren't in the source material, do it. If you want to put a new spin on a character that already existed, cool. Ned has traits of both Ned Leeds and Pete's Ultimate Spider-Man best buddy, and that works. Flash Thompson has some significant changes, but they work in the context of the film, and Flash fulfills the same purpose to the story, so its cool. However, using a name for a bait and switch tactic on a plot point, especially when it only works for people that are more familiar with the source material, bothers me. It's like actively punishing people for knowing the source material. Don't overly cater to them. Make it for a wide audience. Make it your own. But don't play gotcha with long term fans.
Michele is another thing on her own. I liked the character. I enjoyed her random quirks and snarky comments. I loved her delivery. I'm not sure I like the fact that her final comment seems to be a statement of intent that the whole point was to take bits of Ultimate Gwen Stacy, fuse that with Mary Jane, kind of, and thus eliminate Mary Jane and Gwen Stacy from ever showing up in this version of Spider-Man, because they both committed the cardinal sin of appearing in the previous two versions of movie Spider-Man.
I'm not sure how I feel about a major plot development for Tony's character being reversed and moved in the opposite direction essentially as a joke. Also, how exactly to the Sokovia Accords work, again? We're moving into comic book Civil War levels of confusion on how the SHRA actually works. Is Spider-Man registered just based on Tony vouching for him? Is that really allowed? And when Spider-Man goes off without Tony's permission, how is that different than Cap going off on his own? Shouldn't Tony be less worried about the personal level of Pete not being ready and putting himself in danger, and more worried about Spider-Man causing an international incident and needed to have the Avengers called in to throw him into a cell at the Raft? Its like the narrative is super attached to the MCU in places, then really fuzzy in others.
Wet-Blanket Bonus Round!
Individually, I think all of the movies work well enough, on their own, however, there is an obvious upswing in overt comedic moments (not just one liners or humorous situations) from Doctor Strange to Guardians of the Galaxy Volume Two, in this movie, and, from the looks of it, in Thor Ragnarok. I want the Marvel movies to take themselves less seriously than Man of Steel or Batman versus Superman, definitely. But when something feels like an identifiable pattern, I start to worry about how well it serves the individual story, and how much is a studio identifying a difference between their product and another, similar product, and overplaying that difference. To be clear, it's not the comedy in any one of these movies I'm complaining about--its that when you watch them in a row, you can see a pattern developing.
So, What IS Wrong With Me?
Part of this is just that I'm too invested in the character. I've seen too many iterations, and have too many expectations that I'm bringing to the movie. Part of this is I know too much of the "meta-story" of the movie, and how much they want to avoid the previous two iterations, and how the interaction between Marvel Studios and Sony Pictures is affecting what's in the film.
I like the movie, overall. I just wanted to like it more. Given how much I like some of the people and how well they owned their overall roles in the movie, I wanted the whole to come together for me in a more substantive way.
Bonus Brownie Points
Another "not sky hole" ending for a super hero movie!