I started re-watching the trilogy (just saw SM2 tonight), and it still holds up really well IMO. While the TASM movies have a few details that they get really right, as well as better effects (because they're newer), I think what really makes the Raimi movies better for me, is the filmmaking. Sam Raimi is IMO up there among the 25 best directors out there, and he really knows how to put together a great movie. His movies have a lot of memorable parts that the TASM movies lacked. Best example would be Uncle Ben and how they handled that. In SM1 when he dies (after the powerful speech earlier), with Peter sad, angry, suiting up to the music of Danny Elfman, that's just great filmmaking. When the same event happened in TASM, it wasn't nowhere near as powerful. Webb is an OK director, but Raimi is a great one, and that's the main difference for me.
Even SM3 which gets a lot of hate, still has a lot of great filmmaking. You could tell Raimi wasn't happy about Venom, and some of the "Peter gone EMO" scenes felt like Raimi flipping the finger to the producers. In retrospect it could have been better, but it still has good filmmaking in it. The birth of Sandman was really memorable, and I liked the switch-a-roo with Peter finally catching a break, and the tables turning with MJ experiencing tough times.
Also, as much unpopular as it probably is, I love Kirsten Dunst. She doesn't get to display much in the SM movies, and her role is pretty much limited to being saved, but she is one of my biggest movie crushes.
