But if you only want to MITM the connection used by 'pip' to install python wheels - that doesn't check for CT records at all.
It's all rather hypothetical and unlikely, but you could certainly try attacking something like downloads.openwrt.org¹ like that — especially if you can tell apart the TLS client in opkg from a normal browser.
(¹ luckily, OpenWRT and most other package repos don't actually rely on HTTPS for package integrity and authenticity. And OpenWRT would be the most susceptible due to the "exotic" TLS client stack, if any.)
No, the cert can be issued with no (or invalid/junk) SCT and will work fine with clients who don’t check SCT, which is most non-browser interaction.
Am I missing what you mean by monitor?
My point is more that as a user of a high-level library like reqwest, I'd like to talk safer defaults when root CAs are in use