The heal will regenerate 50% of his hp if you max it first. Not when he is max leveled though, but he should have good lifesteal around that time as well. Maxing the charges 2 times + the lifesteal from the enemies is enough to fully heal him.
He is not good in early game, unless you play against noobs who think they can beat him in 1v1 melee combat. He is very easily harassed in the beginning. The exception would be if he is equipped with crit runes, then he can be moderately dangerous if you don't harass him properly.
Olaf never got a major damage reduction, at least not in the last month.
His two most recent updates:
Undertow now deal physical damage instead of magic damage
Vicious Strikes health scaling changed to 0.5% at all ranks from 0.3/0.6/0.9/1.2/1.5%
Vicious Strikes base damage changed to 10/17/24/31/38 from 12/18/24/30/36
Ragnarok damage reduction reduced to 20/30/40 from 25/45/65
Vicious Strikes health scaling increased to 1%, from 0.5%
Vicious Strikes base damage reduced to 7/14/21/28/35 from 10/17/24/31/38
The health scaling is reduced to 1%, which is like 20-30 damage compared to the previous 30-45 danage, A 10-15 damage reduction per hit, not much at all.
The base damage is reduced by 5-3, not even worth mentioning.
Ragnarok took the only major nerf, and it is defensive. I have to admit that this took a big chunk off his diving abilities, so you have to be a little more careful.
Olaf, Xin and Udyr are all good in their own way. Udyr is the heaviest but deals the least damage. Xin is great at initiating, but he is fragile compared to the other two. Olaf deals a bit less damage than Xin, but he is even heavier than Udyr when his ulti is turned on.
Olaf is best paired with a ranged harasser imo. What he lacks is the ability to harass and damage the turret, so it is good to have a ranged champion nearby to do that. He acts as protection for when the enemies are forced to counter (or lose their turret).
Olaf was a jungler, a fairly decent one as well. Now when they nerfed jungling to hell he's simply not worth it anymore. And the nerf to his skills may not seem like a lot, but it's very noticable when playing him.
There's one good jungler left, and that's Warwick. It just takes too long for other heroes to jungle nowadays for it to be effective.
Fiddlesticks can actually jungle pretty decently, but it's only viable in solo-queue.
Jackal is part of the same family, but it's not the same.
It's not totally, but it's kind of like saying a wolf and a dog are the same...
Vladimir is an amazing mage carry into late game. He gains great damage and survivability as well as being amazing in team fights with 3 AoE focused abilities. Since late game is all about team fights, he's pretty much up there with Veigar as a late game mage carry. (Veigar and Vlad are my Mage Mains atm, and if you count it, Singed.)
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It's all been said. The pun, the not so funny joke, the phrase, something about oneself, the not so random picture.
Vlad deals insane AOE damage in late game (3 AOE spells), and even more if he is not focused. Fully stacked Tides of Blood spamming is nasty. His survivability is not good after he used his pool, but he is definitely able to take a few hits. It is especially helpful to survive long enough after a stun to use said pool. He is one of the easiest to score a pentakill with.