Hi, I started picking Olaf in the jungle recently, and have been trying some different runes/masteries set ups in the past week.
So far what has worked for me in Gold V division is:
Smite and Ghost on summoner spells.
Runes
9x attack damage reds
9x armor yellows
3x flat magic resist blues
6x flat cd blues
Total Stats:
4 Magic Resist
15 Physical damage
9 Armor
5% CD
Masteries 21/9/0
Offense Tree
1 pt Double-Edged sword
4 pts Sorcery
1 pt Butcher
3 pts Brute Force
1 pt Expose weakness
1 pt Spell Weaving
1 pt Martial Mastery
3 pts Executioner
1 pt Blade Weaving
1 pt Dangerous Game
3 pts Devastating Strikes
1 pt Havoc
Defense Tree
2pts Block
2 pts Tough Skin
1 pt Unyielding
3 pts Veteran's Scars
1 pt Juggernaut
With this set up you'll start the game with roughly 80 ad and 10% cd, along decent tankyness. My usual jungle route starts with Krugs or Gromp, depending on wich one is closer to my bot lane, after that i do a full clear, ie. If im Blue side, I'll start Krugs, then red, raptors, wolves, blue and gromp, and back to base. After this full clear, you'll be lvl 4, and be able to buy your upgraded machete (I used to go chilling smite, but have had better results recently with the skirmisher one (red one) ).
As for skills, you can start Q or W. Personally, if I know im not gonna be invaded at lvl 1, I start W, since you end up killing the first camp roughly at the same time if you had started Q, with the exception that starting with W, you'll have more mana, since you'll only use it once for the first camp. I max always Q first, for faster clears (Olaf has one of the fastest clears along the likes of shyvana), then I max E second, and leave W for last, since it's a one point wonder skill.
One thing to notice with the way I run him, is that on the first clear I dont use pots at all. The lower hp you have, the faster you'll clear with your aa's + Q. The only exception for this is when I'm facing a champion that's generally good at counter jungling this early in the game, such as Evelyn, Lee Sin, J4 and so.
After the first full clear, I get the upgraded machete, basic boots and 2 hp pots. With this, I solo drag at lvl 4 if I know the enemy jungler wont be around the area. I start drag around the 5 min mark, and get it by the 5:27-5:30 mark. You'll only need 3 out of the 4 hp pots you'll have (in case you didnt used any pots on your first clear) and your smite. Since your W enhances all the healing effects from all sources whenever it's up, it affects your hp pots as well, making it possible for Olaf to do drag this early. You'll end up with around 280 hp by the time you kill dragon, and will have an extra pot on your pocket. From here, you can either go back and heal, use your pot and gank mid or bot, or simply power farm your jungle camps until you see an opportunity.
My general build order is:
*Upgraded machete (skirmisher as of late) + basic boots on the first trip back to base.
*Finish cynderhulk
*Sightstone (basic one)
*Black cleaver, starting with Phage
*Finish Ninja Tabi boots (mid game i go for distortion enchantment, for the lower CD on ghost) (90% of my games i get this, unless the enemy tram has +3 ap champs)
*Deadman's plate, starting with Giant's belt most of the time, to make use of Cynderhulk's passive.
*Spirit Visage, starting with Spectre's Cowl for the magic resist.
**If the game drags up to this point, I'll sell my Sightstone, and get one of the following items depending on the situation:
--Titanic Hydra if im surviving teamfights long enough after I dive to the backline of the enemy team, in order to increase my damage and have more hp.
--Randium's Omen if the adc carry/carries of the enemy team are killing me too quickly.
-- Sterak's Gage if the APC of the enemy team is blowing me too fast while diving.
-- ZZ'Rot portal if I just wanna get tankier overall, and my team doesnt need the extra damage I could bring with Titanic Hydra.
As for elixirs, I always go with the Elixir of Wrath, the offensive one for AD champs. Aside of the extra ad it brings, what I really value from this item is the 10% heal from all AD damage you do, this includes your Q, and not so sure, but probably from your E's true damage as well. Paired with your W active, and you'll have more than enough life steal to survive a longer, compared to getting a Ravenous Hydra in your build and losing hp or other stats from other items imo (this is why I preffer Titanic over Raveous in case I wanna go for one of the 2 Hydra choices.
Lastly, regarding the upgrades from machete, I ran 3 or 4 times Trailblazer on my build, but whenever i ganked , I felt I was lacking a key spell on my playstyle, be it the additional slow from chilling smite, or the 20% damage reduction AND true damage via physical attacks with the Skirmisher one, so this geared me towards picking either the chilling smite of the skirmisher one, and leave behind the trailblazer choice.
As to wich one pick (chilling or skirmisher), as of late, I've found out that the Skirmisher one fits better my playstyle for the following reasons. Early game, your ganks are devastating, even with just the skirmisher smite + boots. Your Q will deal considerable damage on any squishy enemy, be it the enemy mid laner or bot lane + your E's true damage, add on top of that that you'll get 20% reduced damage from all sources from the marked enemy, plus the extra true damage you may get from landing 1 or 2 aa's during the gank. The 20% damage reduction will have a bigger impact mid-late game when the enemy carries start doing more damage to you, and bring some armor or magic penetration on their kits.
I left the chilling smite out of my build, mainly because the slows no longer stack, and your primary and only real way to gank, is via landing your Q on the target, and then follow up with a second one, and land some E's and aa's, along a third Q, if the enemy last this long. Some ppl may argue that the chilling smite lets your prepare to land your Q easier, since the target will be slowed already, but in all honesty, once you get the hang out of Olaf's kit, the distance and speed travel of your Axes, you wont need the chilling smite anymore. Add to that the fact that you will be running ghost (at least I do), along Deadman's plate, and you'll have plenty of speed to catch your axe quickly, in case you missed it, and throw it again if you see the opportunity. Worst case scenario, the enemy burned flash, and it has higher CD compared to Ghost, so it's a win in my book.
Hope I may had been of some help, and keep practicing Olaf in normals before you take him to ranked =)
Regards!