The only real time I can think of where they caused any impact to the end users would probably be when they changed up a bunch of software because of licensing issues -around 2001 or so. That also led to them writing or re-writing a lot of software and gave us pf, too. So I'd call it a net gain, personally speaking.
On the linux front -libc6 and the elf change-over caused a lot of breakage; like you said -I'm not sure if I would call that "drama" or not.
You are on about direct user impact, where a project discontinuing is perhaps an ultimate one (EOL being moved 8 years in advance is almost that).
Regarding OpenBSD, that isn't the only occurrence. You can grep mailing list archives for some keywords. Look at how people like Daniel Hartmeier, Niels Provos, and Wim Vandeputte got treated. Sure, it did not cause OpenBSD to collapse but I would say it was controversy.
That is the best example I can come up with. I do remember Debian libc being broken, as well as the cryptography, but I would not say that was drama.