The obvious problem is that there's nothing between $100/month and $42,000/month.

That's a huge chasm to cross. A moat, if you will.

Anyone who starts out small and grows organically is just going to get choked out, like planting an acorn in a bucket. So why even try?

Maybe that's the intent?

Sometimes I really wonder about this new CEO guy.

I think the enterprise plan is probably intended for established corporations that already pay out hundreds of thousands per month. As developers we're looking at it from the perspective of like "I want to build X on top of the twitter platform" but from their perspective it's more like "I want to sell access to my database to Pepsi and ESPN."