Well, let me preface this by saying that I'm a bad player.
Last night, I tried Olaf JG for the first time and I really enjoyed playing him. When I went to look at champion.gg, I noticed he had a really low win% and was wondering if learning to play him was a good idea. I watched Worlds and saw him a few times. The most notable play was when (can't remember team) took Olaf, ulted into 5 champions fighting baron and he stole baron. That was when I was like, "Oh hm... that's pretty badass. Maybe I should try him someday."
I realize that Olaf has no CC and that he falls off late game. I looked at his win% after 25 minutes and it's atrocious. However, at my ELO/MMR, games don't typically last that long before somebody is already giving up.
And one thing that was really amazing was that Olaf easily solos dragons and rift early game if nobody on the enemy team pays attention. With dragons spawning sooner, he seems like a great pick into that kind of thing until I come across better players.
What I'm looking for here is some overview of when Olaf is a good pick and what to build on him. Because, honestly.... most of the stuff I've found on Google is outdated information. Maybe I'm just looking in the wrong places.
And if you look at my match history, yes I suck! I'm bad. I get it. People never fail to remind me.