Aren't we (NetBSD) a user of fastly.net? This looks to be a problem with them - perhaps someone who has contacts there can have them look in to this.Why do you think this is a problem with fastly? The links you cite are all pypi ones, not NetBSD ones.
host files.pythonhosted.org files.pythonhosted.org is an alias for dualstack.r.ssl.global.fastly.net.I'm just thinking that it's easier to talk to some of these companies as a customer than as a random person on the Internet. That's definitely true of, say, Google - there's literally no way to contact a human at Google if you're not a customer. Maybe fastly.net is more receptive.
John