You counterjungle in several cases:
1) You know you can take their jungle without running into anyone. This happens most frequently when enemy jungler has just died or pops up on the map in another lane, giving you a window of opportunity to manipulate their jungle.
2) Your jungler/team is stronger, giving you the confidence to win fights even if you do run into someone. Examples of strong junglers are shyvana, udyr, and skarner.
3) If your opponent is absolutely dependant on certain buffs, like amumu on blue. You also contest their blue buff if their mid (like anivia or ryze) really needs it as well.
Magic resistance stacks additively, and is calculated via this formula (assuming positive MR):
Damage taken = Raw damage * (100 / 100 + MR)
25 magic resistance → ×0.8 incoming magic damage (20% reduction).
100 magic resistance → ×0.5 incoming magic damage (50% reduction).
source
Magic penetration is applied in this order:
- Flat magic resistance reduction
- Percentage magic resistance reduction
- Flat magic penetration
- Percentage magic penetration
source
Magic penetration stacks multiplicatively. Void staff (40% magic pen) and the Arcane Knowledge mastery (10% magic pen) together equal 46% magic pen. source
We can see that the types of magic pen are very important, because buying flat magic pen (sorcerer's shoes) makes % magic pen (void staff) less effective. Unless the enemy has a lot of MR (ex: Galio), it's not worth it to buy multiple types of magic pen.
Compare some examples with a base MR of 30. With 0 magic pen, 100 magic damage does ~77 damage. With Arcane Knowledge, we ignore 10% of 30 MR (27 MR total) and deal ~79 damage. With sorcerer's shoes, we ignore 20 MR (10 MR total) for ~91 damage. With shoes and arcane knowledge, we ignore 20 MR + 10% of 10 MR (9 MR total), or ~92 damage.
We can see that for low values of MR, increasing Magic Pen provides very little gain. It also shows how effective flat MR is vs low amounts of MR, whereas percent reduction is not.
Now let's consider a large MR, say 200 and 500 magic damage. With 0 magic pen, that's ~167 magic damage. Arcane Knowledge reduces the MR to 180, or ~179 damage. Sorcerer shoe's are the exact same here. With shoes and arcane knowledge, we ignore 20 MR + 10% of 180 MR (162 MR total), or ~190 damage. If we add a void staff to these 2 (discounting it's bonus AP for simplicity), we get 200-20-72-11 (97 MR total), or ~254 damage.
It's safe to say at this point that unless the champion is stacking MR, you'll do more damage buying AP instead of Magic pen. A notable exception to this rule is Soraka, because her passive provides a substantial MR aura.
tl;dr: Runes, masteries, and sorcerer's shoes provide enough magic pen vs most champions. Only buy additional magic pen if the enemy champion has over 100 MR.
Best Answer
I generally max my W first for three reasons:
The reason I get it to harass, is because you can shoot your opposing lanemate through his minions, and it makes it slightly harder for him to farm with that debuff.
The buff it provides your teammates when pushing towers down is paltry at best if you max it second. Maxing it first, however, means that it will be Lv 4-5 by the time your towers are going down. Its a very good utility spell for the team!
His W makes stacking his passive extremely easy early game. If your support is doing it right, you can get 2-3 stacks on your passive with just one W! That means you're able to harass or farm at a +30% rate over your opponent BEFORE taking into account the debuff placed on him by said W.
Sure its not nearly as spammable as his Q, but you use less mana when harassing for slightly less damage, but the ability to harass through minions where he thinks he's safe from your wrath. Besides, the buff/debuff (damage too!) scales well with levels, whereas the Q only scales damage (the CDR doesn't scale at all, so why bother maxing it first?) and isn't as useful early game (in my opinion).
Hope that helps!