On
question 1: I agree with what's been said, I think the hand is a straight keep and the most likely play is vamp for Academy.
But I'd like to drill down just a bit more: which artifacts do you play on the first turn, and when do you cast vamp? I think obviously you want to play the jet and save Vamp until your opponent's turn, just in case you need to switch the plan up a bit. But what about the Crypt and the Pearl? Playing them now gives you protection from spheres and chalices, but reduces the storm count, costs 1.5 life, and gives an intelligent opponent information on which they could probably conclude that you were going to play academy. I think that the answer really depends on what deck you're up against, and not knowing that, I'd probably take the middle ground: cast Jet and Pearl, hold Crypt, and pass the turn. I'm very open to being convinced otherwise on that point however.
On question 2First, I would really like to know which mana I have in play that is tapped out. And I agree with Steve that I am curious why we bothered getting into this counter war over Yawg Will.
Putting that aside, we can assume you will be taking 6-8 damage on your opponent's turn.
I don't think this is right. The opponent has an Orchard in play, so he will be pumping Helkite to attack for 9, and as much as 10 if he plays another orchard.
But, maybe the opponent isn't about to get Helkite, maybe it is only six. The truth is, there are a LOT of variables left. I would draw cards as conservatively as possible, and plan to use time walk and draw more next turn after I have more variables resolved (what opponent attacks for and what my first few draws are). With the yard as stacked as it is and his counters depleted, I think there's a very very good chance I win the game so long as I get to untap with the cards I necro'd for, especially if I can walk and draw more. Thus, I'd be very conservative and leave 3 life for grim/vamp+draw/seal+draw as well as 10 life for helkite damage, that means I only draw 4 this turn.