I'm the biggest fan of Elon there is, I'm pretty sure, but this still makes me nervous.
The timescale is bullshit-- the past two failures have both pushed things back a ways, and at this point I'm not optimistic there won't be more failures soon (although I strongly believe they'll succeed completely in the long term regardless). Things would have to go perfectly for this timescale to actually happen.
But what really makes me nervous is the thought of it going wrong and people dying. That would be pretty terrible. I feel like they need to do a lot more testing before they can send anyone around the moon in a mere 18-20months. That's just too soon. F9 is still having confusing failures after years in service. Falcon Heavy hasn't even flown once yet, nor Dragon 2.