Originally Posted by HTupolev

You're cheating your own comparison by incorporating the discount. The market is in a much different state right now than it was when you bought the 2014 bike. And $4000 in 2014 is about $4500 in today's USD.

The $4500 Caledona is not "the base spec." The lowest spec is the $2900 105-equipped version.
There's also a $3500 variant spec'd with mechanical Ultegra. Considering that your 2014 bicycle was not spec'd with Di2, it's arguable that the closest comparison in the Caledonia's lineup is actually the $3500 mechanical Ultegra variant. Compared with your 2014 S3, this variant does lack a carbon aero seatpost and has less-fancy wheels with a shallower section, but it's also pitched as an allroad bike and is $1000 cheaper when considered in 2020 USD.
The $4500 variant also lacks these things compared with your S3, but that's because they're specifically hitting you with a big penalty for Di2, which your S3 does not have.

I'm confused as to why you think that the $6500 Caledonia 5 variant with e-shifting and an integrated cockpit is at the same spot in the food chain as your S3, which came with neither of these things.