1. "Why HSR before local trains?"

This is really two questions. First in terms of trip shift, it seems plausible that HSR will have an easier time shifting air and long car trips to train than a massive investment in subway expansion would from shifting car trips to transit.
This is because the US is a developed country and thus land use patterns switch slowly especially without strong carrots, and nobody is interested in making car drivers pay more right now.
Shifting mode in intrametropolitan travel seems to be at best around 10 points a decade from car to transit. HSR between SF and LA for example would probably annihilate plane overnight.
2,"Will HSR make America more connected?"

I'd just like to address an error of fact here. Noah cites Japan's high Tokaido Shinkansen fares as proof planes are cheaper than trains. However what you're seeing there is the use of fares as a demand management device.
CAHSR always planned for the train to cost less the plane, and in fact HSR costs less than planes in Europe. After all there's a reason there are functionally ~0 Lyon-Paris flights.
As to Noah's actual point that HSR is a, " point-to-point connection," that's just not true, and I'm surprised Noah says it. HSR even in France (by far the most airline like HSR network) stops at small towns that are on the way.
The Japanese Shinkansen of course does stop in small places. Places like Izumi, Kagoshima (52k); Itoigawa, Niigata (41k); and Aomori (310k) have stops!
3. "Who will use it, and how will this benefit the economy?"

I have no idea if business travel is dead, but I'll just point out that every new communication technology has not in fact killed intercity travel. Intercity travel has only become more popular.
4. "Why haven’t we been able to do this so far?"

First, the CAHSR has arguably been a better run boondoggle than the standard piece of transit construction.

@alon_levy is far more comprehensive than I am, but I'll point to two things.
1. Environmental legislation that doesn't actually protect the environment, but drives up costs to fend off litigation, and lengthens construction timelines.
2. A lack of a robust bureaucracy that's technically proficient in what is needed to get projects like these done.
5. "Is HSR monument-building?"

God I hope not. At best it's really a project that massively facilitates intercity transportation between many of our largest cities. The US has the second best HSR corridor in the developed world (Boston-Washington). It should be useful.
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