I got obsessed with Paul Simon around the same time I got obsessed with MK, about aged 13/14.
Over the years my interest has waned, partly because of a lack of productivity, partly because of the diminishing quality of his work IMO.
I've always generally preferred his solo work and would rank his solo albums like this:
Still Crazy After All These Years (an absolute classic and one of my favourite albums ever)
Graceland
There Goes Rhymin' Simon
Hearts and Bones
One Trick Pony
You're The One
The Rhythm Of The Saints
Paul Simon
Surprise
I've only listened to the new one once so not sure where it would go.
One thing I would say about Simon is that he is one of my favourite guitarists ever. He's not far behind MK IMO (seriously). If you go and listen to the intricate and imaginative fingerpicking parts from his early career, well, they are spectacular. Just my opinion, but I would rate him as a better guitarist than Clapton, who I get bored of easily, playing the same blues licks all the time.
For Simon and Garfunkel albums I would go:
Bridge Over Troubled Water (another stone cold classic)
Bookends
Sounds of Silence
Parsley, Sage Rosemary and Thyme
Wednesday Morning 3AM
With Dylan, I liked him as a kid but as I have got older I have come to appreciate him more and more.
I think it is absolutely fair to compare the two - they are both two of the greatest songwriters of their generation.
Simon has always been more "pop" orientated with more of an emphasis on melodies.
Dylan is more about the lyrics.
The production of Paul Simon's records have been consistently excellent throughout his career. Dylan records are all over the place, although I will concede that it can add charm. Some of his greatest records have mistakes all over them - listen to the organ part on Like a Rolling Stone. Al Kooper was a guitar player really and either he didn't know the chords or was hesitant about playing them because he is a few beats behind on the verses. Vision of Joanna, which may be my favourite record ever, towards the end the band play wrong notes all over the place as they don't know Dylan is extending the verses. A big difference to the intricate production on, say, Bookends.
But as I say, I lean towards Dylan more these days, not least because of the truly excellent Theme Time Radio Hour series. I'm still trying to work through them all but they are truly brilliant. Dylan is hilarious on them.
PS Seen Simon live 3 times (once with S&G) and Dylan once, Simon is better live, if more predictable.