I've grown up with Spider-Man as my favorite superhero (and he still is) and if anything he's one of the few superhero properties I give any shit about. Couldn't care less about Iron Man, indifferent on Batman, I like Captain America, Superman, and Hulk, etc.
The Raimi trilogy is by far the best of the three iterations of live-action Spider-Man. I don't even think it's close. The cinematography, the soundtrack, the action scenes, most of the casting, and even the effects are absolutely perfect (or at least as perfect as they could be for the time they released, its not half-assed like MCU effects). I regularly rewatch 2 and I love it just as much as I did (hell probably even more as I got older) when I walked out of the theater in 2004. Its easily top 3 best super-hero movies, I don't think anything else really has the same sense of inspiration or heart to it in the genre. Its an excellent film all around. I think my only real overall criticism of the Raimi movies is that Mary Jane is not written very well, but she's still nowhere near as insufferable as MCU MJ (at least until Spider-Man 3). A lot of people dismiss Tobey as being mopey/meek, but they don't realize that the original Stan Lee/Ditko iteration of Spider-Man from the 60s-early 70s (which I'm sure is what Raimi grew up reading) is almost exactly like this. Peter in the early issues was not a jokey, snarky jester like he is in later portrayals, he's a lot more serious and calculating, which Tobey's Spider-Man represents very well. As a matter of fact, I'd say the Raimi trilogy easily is the most understanding of the source material, or at least Stan Lee's Spider-Man. It really understands comic book camp and sillyness to a T without being overly meta or anything obnoxious. It just plays it up in all its glory and I absolutely love that, it makes the movies feel very genuine, even with 3 being much weaker than the first two.
The Webb movies are weird because I really appreciate Andrew Garfield's passion and I definitely feel like he got screwed over (he's easily the best actor of the three) with the writing. The first Amazing Spider-Man is a genuinely good movie, like a 7/10. Its not amazing but the effects look and have aged great and I appreciate them still pushing for a lot of practical work. The writing is fine and Gwen is easily the best love interest out of the three movie series because she's actually supportive and not whiny/snarky to Peter constantly. Gwen is easily the best part of TASM1 and TASM2. I do think TASM2 is mildly overhated, its not awful per say, but its a huge mix of great stuff with absolutely awful stuff. The effects are insanely impressive and the action scenes are unique and interesting, but the writing is absolutely terrible for the most part and is clearly juggling between Webb's vision and the studio's vision. imo its like a 5/10. Andrew's Spider-Man is very clearly inspired by early Ultimate Spider-Man, which is fine, Peter is a bit more awkward and prick-ish in them which fits what they were trying to go for.
Now the MCU stuff, is super polarizing. I loved Tom's entrance in Civil War, but I absolutely despise how they treat him after. Imo Homecoming is easily by far the most overrated MCU movie by a country mile. I actively dislike it more and more each time I rewatch it. I think it is insanely unfunny, poorly shot, has pretty terrible effects work in it, I don't like Peter's friends at all (Ned is annoying as fuck in all three movies and his school friends are equally pointless and unfunny), and MJ being a snarky ass makes her completely unlikable. This isn't even really including how I think it completely misunderstands Spider-Man as a character; he was always an independent loner-type character until Civil War and this released. Instead in this movie (and Civil War to some extent) he's bumming to be a sidekick to a rich guy, which is kind of just the complete antithesis to the humble, street-level, loner type Spider-Man has always been historically written. I fucking HATE the conversation halfway through the movie where Peter openly admits he's nothing without the suit, its so incredibly un-Spider-Man, even if its technically supposed to be a different type of "origin story" for MCU Peter. The only thing I like about Homecoming is Vulture. Michael Keaton is great, that's literally it. Far From Home is fine if forgettable, its definitely better than Homecoming for at least having better action scenes and less Ned/MJ bullshit in it (at least up until the end). No Way Home is definitely the best of the three, and its entirely carried by the Raimi villains + the course-correction of Tom's Spider-Man. I think if anything No Way Home is pretty strong evidence for how awful quippy dialogue is, as both Doc Ock and Goblin are clearly written with more Raimi-esque dialogue (campy and direct), and as a result they come off as significantly more sincere and menacing than like 95% of most MCU villains. Plus seeing Tobey and Andrew again was amazing, Andrew really killed it and showed everyone what he was capable of with good writing. Its probably one of the only modern nostalgia-bait films that actually works very well, its extremely respectful to what its calling back to. I genuinely hope with No Way Home's ending we never see Ned or MJ ever again, I'd begin to genuinely love Tom's rendition if he actually had to do things on his own like the ending was suggesting.
Side note for the Spider-Verse movies: imo gorgeous animation, extremely generic/flawed writing in both movies. I'd give both of them a 6/10 for different reasons. Very overrated but I at least appreciate their ambition.