The problem with the Raimi movies is that none of the characters were particularly interesting. I don't recall a single time that I ever cared about Peter Parker's problems.
Agreed with two exceptions: Otto Octavius and J. Jonah Jameson. The first had a rather large part, being the main baddie, and I honestly loved the way he was portrayed in the movie as well as his character. The latter, however, was a minor role, but he was a good character. I do agree that I didn't feel much connection to Raimi's Pete the last time I watched it (which was pretty recently), with one or two exceptions throughout the films.
Also why did Spidey have to climb up buildings and get all the crane drivers in New York to help him when he got shot in the leg? The stupidity of that scene still blows my mind. His leg!
I think it could be justified saying it was more of a straight shot to Oscorp Tower than having to swing across buildings, especially because his limited amount of time. I think the focus was more on showing how much impact he had on the common folk (or at least construction workers) that they weren't evacuating like all the other screaming civilians, but staying to help their Friendly Neighborhood Spider-Man. To create a more emotional rise or something like that.
On the reboot, I really did like it a lot. Spidey has always been one of my favorite Marvel superheroes, and I really like the way this movie went. Sure having a giant Lizard trying to turn everyone else into giant lizards is a bit ridiculous, but remember: it's a movie based off of a comic series. Comics can get pretty wacky, corny, and at some points you just facepalm, but you love 'em regardless. Or maybe it's just me.
One area in which I think the Raimi movies beat Webb's reboot was the score. I don't know if it's the nostalgia of seeing it when I was 5 and thinking it was the coolest thing ever, but every time I hear that score I just get pumped. Danny Elfman did a fantastic job, and made a really memorable sort of theme. I liked the reboot's score, but it just wasn't as memorable.