Yeah, that one goes right in the trash. For a PB to list so many silly items like this, and charge so much for them, he should either be embarrassed, or proud some sucker actually goes for that.
As others mentioned, just a few highlights.....
$3k for caulk? Really, caulk?
$7k for Intellitouch? Really? The lowest automation, and very outdated? Sure there should be some markup, but to even suggest installing that on a $300k+ pool is absurd!
As others mentioned, this is either a "I don't want the job but I'll do it for this price", or somehow he has misread the neighborhood and what people should be paying for a pool. On top of that, what happens where there are change orders? What happens when you need to pay for landscaping, or furniture? A $500k pool that is 4' deep and 23 x 40?
File that one in the recycle bin, and find yourself a reputable builder who is upfront and honest about the process and pricing, this builder's proposal is neither of those.