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I'm actually working on adding the Threats and Synergies to all of my guides. This Olaf one will be the last; my Kayle guide is just taking priority and the longest to do them for.
Except for that, it's more than questionable to even list pure lifesteal build like Ravenous Hydra + Blade of the Ruined King + Death's Dance. Main reason for that is, that those items are very expensive, yet they can get countered quite heavily by Executioner's Calling or Bramble Vest, that are very champ items compared to it. Obviously, there is as well Morellonomicon. You might say, that you still heal quite a lot - yeah your healing isn't disabled, but it's crippled very badly... combined with the fact, that you are quite squishy, it just makes build very awkward and dependant on opponent's inability to understand how to build items to counter his opponent.
Yes, I agree I shouldn't have included every item as a possible choice; I've edited the guide to address the issues you mentioned plus more.
I really like Death's Dance as a 5th or 6th item (or 7th after selling boots) on Olaf because of its bleed passive. It lets him live a little bit longer in fights where he has to frontline or dive the backline.
In the offensive build, I've swapped Blade of the Ruined King for a defensive/different item.
Again, thanks for the feedback!