Not sure if it helps, but I looked up the chord sheet for this song, and I immediately "waved it off" just based on what I saw. I'd never be able to remember that chord progression. (You're talking to a bluegrasser here, by the way. Any song that has more than 5 chord changes has to go the extra mile and
really convince me as to why I should learn it.
)
I've been playing for more than ten years, and it would be very difficult for me to play this song. No way I could learn it within just one day.
So I'm very tempted with voting for your first hunch, that you're overtaxing your abilities at his point.
Another thing that I noticed when listening to Paul Simon's recording on YouTube is that there is almost no guitar in this song. It's mostly keyboards.
So I'm wondering whether Paul would actually have written the song the way he did had he written it for guitar? It's of course much easier to finger a bunch of complex chords on the piano than it is on the guitar. Just a guess, though. I'm not familiar with how he wrote this song.
And just on a side note: I usually never aim for playing a song
exactly as the original, because I find that pointless. I'm thinking from a performance standpoint: Who wants to hear random guy play a song
exactly like [insert artist name], except he isn't ][insert artist name]? For me, the answer is: no one. I find much more reward in trying to capture the essence of a song and adapting it to my own musical language and artistic expression. If I play a song exactly as the original, it will never amount to anything more than a cover. But if I make it my own in some way that is convincing to the listener — and more often than not, that involves simplifying — the piece becomes something much more valuable.
The vast majority of my repertoire are traditional songs and American roots music, in other words, songs that have been played to death for decades, if not centuries. Yet, on more than one occasion, I have had others tell me, "Oh man, that version of Shady Grove that you played there, that was really cool." In all of those instances, I don't remember doing anything fancy. If anything, I simplified the original or more commonly known version so as to bring it down to my level. But I did add my flavor or feel to it.
Sometimes less more.