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If you're going undertow as your first ability to level then armor pen & cdr is the best route
If you're going reckless swing you should be going tanky
If you're going vicious strikes then the itemization (rushing phantom dancer) you start with makes sense.
But you are leveling vicious strikes last...
My advice to building Olaf in this format would be to try vicious strikes first. So much of the combat is melee smash melee that vicious might actually work. If not...I think you need CDR/Armor Pen to throw your ax more- a brutalizer would work. Ghostblade also would help mobility and attack speed.
Edit: Better yet, why not a spirit visage. I give health, mr, and cdr all useful for your early game and it improves lifesteal on top of it all.