Wait, there's a question? The second is obviously crazier.
Watch out -- edge cases incoming. Can you think of when the first would be crazier?
The real question for the edge case experts is to find a situation in which each of them is the best play of all possible plays.
You want that to be the best play? Alright.
You had just played Golem and drawn Lookout/Moat (don't ask what the heck is going on in this deck okay it just is). You have in hand a Scavenger, Vault and two Estates are ahead by 7 points and the Colony pile has 1 Colony left. You decided to resolve Lookout first.
How do you guarantee yourself $11? You need the extra actions, and the Platinum in your discard. So you trash Tunnel (2 points is meaningless), and put Fortress on top of your deck to be drawn. So you draw Fortress giving you Scavenger, Fortress, Vault and two Estates in hand. You Fortress, then Scavenger, putting Platinum on top of your deck, giving you $2 and Vault, Estate, X and X in hand. You play Vault, drawing Platinum and discard the other four cards, giving you $11, you buy the last Colony and win.
There. Edge Case'd