Which ironically makes the Internet more surveillable, because now every single connection has to hit some TLS-terminating origin and can't be cached at the edge of our own networks. Don't confuse security with privacy.
Of course it can. Just not without the user's knowledge and consent. Let the user load your CA and you can cache and repeat whatever you want.
In practice, those caches were all done for malicious purposes, usually for injecting ads and selling tracking information through injected headers.
Those shared caches were monitored just as strongly, if not stronger, by the people doing internet surveillance.
Can't cache interactive content which is probably more invaluable than static. HTTPS is overall a massive win, which is why NSA wanted to surveil it in the first place.
What???
The internet is only more concentrated because most people choose price and convenience over a foolproof level of security. The cost/effort required to surveil traffic in coordination with TLS-terminating CDNs is multiple orders of magnitude higher than the effort needed to throw some high-Tbps middlebox in an IX rack to siphon every packet passing through it.
Let's be realistic, very few networks had speed-improving caches that weren't surveilled. Transparent proxying was most often used to inject malware and fourth-party ads, instead.