Not Updated For Current Season
The masteries shown here are not yet updated for the current season, the guide author needs to set up the new masteries. As such, they will be different than the masteries you see in-game.
The First "Blood"
Bad idea ... The cooldowns are starting with 15+ seconds, so you have to attack with your normal damage ... So you need a great partner, who makes the most damage.
You can buy the Ionian Boots of Lucidity or the Sorcerer's Boots.
Ionian Boots of Lucidity:Vladimir has a lot of cooldown, so is "Cooldown Reduction" very nice.
Sorcerer's Boots: Vladimir is going to make more damage ...
Why build on HP?
Vladimir's Passive: He gets for HP - AP (Ability Points)
He gets for AP - HP (Health Points)
So you also can buy one Warmorg's Armor more, for the Spirit Visage, cause you'll get a lot of AP for the Warmog's Armor.