Homebrew is using bintray for precompiled packages and I also don't have XCode installed (only the commandline tools). And I never had problems with Homebrew because of OS upgrade. This "issues" are all solved IMHO.
OS upgrades nearly always require re-installing more than half of my packages, which can only happen after fixing various command-line tools, which can only happen after updating xcode. And some things perpetually link to old versions, and the problems crop up over the next few weeks. And running a pre-release of OSX can cause looooots of complications. Generally though, for release-channel people, yes - homebrew has done a remarkably good job.
Obviously YMMV, but in a Dockerized world the required steps would be: 1) upgrade the OS, 2) maybe update Docker
