Good comment and fair point. I cant really respond well without seeing a replay (and happy to), but generally speaking:
Olaf is best when lanes are high damage and he can use his Q to slow them down and his E to drop large amounts of health while letting lanes finish them (or using his E as a finisher).
This is based on your lanes usually only having one tank (usually sup or top) and you really want 2, he can go DPS if your a tanky team by swaping a few items. Drop Randuins or Runic based on their team comp and who is ahead and get a bloodthirster as well as your hydra/atmas.
Armor Pen passive is good, and your AD boost from your W is quite large later on and when you get Atmas, you should have no problems with not enough AD.
His passive attack speed boost as he loses health was factored in. You can run down health safely when you have alot of it and hit them at a high speed for longer without risking death.
Lifesteal is good all round, with your Frozen Mallet you should have enough damage combined with your W and your attack speed to make good use of it.

Also 20min isnt really the best test of a build. Your build should adjust if your ahead or behind with items that prevent you from losing more, or items that allow you get get further ahead. Build damage when your ahead, and health when your behind.

Well that was a quick 20 minute game. Followed all of your instructions. Score was 2/4/2.
Ummm.... I understand your logic of changing up your runes and masteries because Olaf only has one skill that scales off of AD ... HOWEVER, this mentality of yours sounds like you play plenty of AP carries mid, or Crowd-Control based junglers like Maokai, always worrying about damage scaling and what-not. You ignored 3 very big things about Olaf.
1. Passive armor penetration.
2. Passive attack speed
3. Big life steal buff.
Without the proper damaging items, these passives become useless. I had high hopes for this build but, when it comes down to it, you don't have the damage necessary to fulfill the role of a jungler.

Please keep adjusting your build, I'm very interested in your way of thinking because I have zero creativity when it comes to builds.

I'm going to try this out. It seems you have your reasons for using this specific set up for olaf and you provide it with facts.
Brb 1 hour.

So yeah... i sucked it up and did a real update.

Now we have detail. I excluded all the Math >.<

Updated items slightly and changed runes.

Summoners were ment to be Ghost/Smite. Ult+Ghost lets you run right through their team and kill the carries easily.

Olaf can run 21 utility without it impacting his clearing speed or his sustain early game and is far more valuable mid game.

Wriggles is a great starting item but is very weak compared with getting Black Cleaver early and rushing Warmogs. The key is dont die, these allow you to do that easily, and health is a multiplier for his E.

I usually do it early because im ahead, and selling that and getting Warmogs/Black Cleaver puts me further ahead. If im not doing so well I'd hang on to it till after i get Randuins Omen or Runic Bulwark and cash it in for Last Wisper or Frozen Mallet.

Why would you buy a wriggles to sell it 10 minutes later?
Also why are you running 21 util?
Also why are you running ghost flash with no smite?