I just finished a rewatch of the original Spider-Man Trilogy in preparation for this movie. I plan to rewatch The Amazing Spider-Man movies and Homecoming/Far From Home as well, although i'm really more focused on the older movies that I haven't seen in awhile.On a rewatch, I think the original Spider-Man trilogy was a great look at Peter struggling through being Peter and juggling his relationship with MJ while still being Spidey in the city mostly.
I also think Spider-Man 2 stands up as one of the comic book genre's best films, right along with The Dark Knight, Joker, Logan, and Winter Soldier. If one of the Avengers films were to be put into that category, i'd say it would be Infinity War as I believe it to be the superior film to Endgame.