It's only a matter of time before an intern or an audit guy have it deployed on majorcompany.com and result in a disaster. Symptom includes none of the client ever able to access the site again.
They were only accessible from our network (ethernet or VPN), so we hadn’t bothered with HTTPS before. Oh and we only found out about the issue when Chrome updated and everything broke - it was a fun few days!
Also with HPKP you shouldn't just pin one key. You should pin several keys you own as well as several root and intermediate keys. But I agree it's very difficult to do right and there's still a risk of it failing.
By way of comparison, it has never been a good idea to default to HPKP. Privacy-sensitive sites should be pinned, and if you can't safely manage pinning, that's a pretty good sign that you're not mature enough to engineer privacy for the site either, so I don't have that much sympathy for the argument that it's a foot cannon (this is, of course, very easy for me to say). But if you're just selling coffee beans or scheduling laundry pickups, PKP has always been a very bad idea for you.
The latter example is where HSTS becomes an invaluable tool, since now the only way those resources could be delivered is through a trusted channel, verified by the PKI. The same value is not there for a software mirror, because of the other security safeguards already implemented, removing the need to trust the delivery channel. That said, most still do server their content over HTTPS as well.
It will backfire when the certificate expires, when some clients don't recognize the CA chain, when domains or subdomains don't match the certificate.
Glad there are more reports of this showing up.
In theory, pinning your servers' private keys is actually kind of reasonable, if you generate like two or three sets of backup private keys and put them in off-site storage. And I've long been an advocate of buying at least one backup certificate from another CA just in case your current one gets distrusted.
(And it makes sense from a technical perspective why HPKP supports both of these approaches, but the ambiguity probably didn't help it from a policy perspective).