So, I don’t want to make this all about Bob Dylan, though I’m happy to argue my case a bit. I want to hear about your examples too.
This is about being a semi-contrarian instead of a hater. Someone is worshiped to the skies, and you appreciate him/her as well–but you can’t quite get to the worship level.
My friend and I went through a big Dylan phase when we were in college in the 90s. We both bought a bunch of albums. He got more into Dylan than I did. Over the years, we’ve argued about Dylan. He can get a bit irate and say, “Dude, why do you have to put Dylan down?!”
Well… I think Dylan certainly has (or had) “It”: the ability to convey a sense of depth and substance. (I’m going to keep using past tense here because I think his best work was in the 60s and early 70s.) He seemed “big” in a way that very few other artists have been able. He was innovative, putting folk and rock together in a new way. He could write both exceptional lyrics and melodies. And I even like his unique mode of singing. But I also have caveats:
• There is the air of bullshit about a lot of his songs. This works both for and against him, IMO. A masterpiece like “Maggie’s Farm” wouldn’t be a masterpiece if it made real sense. But a lot of his songs are in that mode: overwritten and a bit “meaning-y,” as I call it. Instead of trying to say something specific, they rely on poetry overload to bonk you over the head and impress.
Moreover, even though a lot of his songs in this mode (and most are in this mode) work as individual songs, his body of work in the aggregate is a bit fatiguing for me. He’s kinda doing the same thing over and over. He doesn’t possess one of the great virtues of the Beatles, which is variety.
• His work tends to be a bit humorless, even when it’s absurdist. The tone of a lot of his work feels the same to me.
• He’s no master of structure. 95% of his songs are verse/chorus. The aforementioned best friend and I combined our knowledge and sought a Dylan song with a bridge: we came up with “Mozambique,” and even there he seems to have stumbled upon the bridge. I guess “You’re Going to Leave Me Lonesome When You Go” (one of my faves) has a middle eight. I’m sure I’m wrong and there are others–please let me know.
• His harmonica playing is genuinely terrible.
• After a certain date, sometime in the early 70s, he really sucked. There are exceptions after that. “Jokerman” is a genuinely great song. But as happens with most artists, he lost it.
So that’s my thought on that. What are yours on yours?

 I’ll be the first to admit that much of their output is extremely erratic in quality.
  I’ll be the first to admit that much of their output is extremely erratic in quality.