Oh god no. Homebrew managing openssh has been the cause of more command-line instability and forced reinstalls than anything else I’ve encountered in the last few years of OS X (sorry, macOS). I’ve started installing stuff from source again just to prevent a cascade of Homebrew upgrades breaking everything.
I sometimes use NetBSD's pkgsrc on macOS because it installs super cleanly in any prefix you like and never, ever breaks the system. It doesn't have everything, and you will occasionally encounter a package that won't build, but it doesn't even dream of taking over /usr/local or disrupting your system. You could install it into your home directory if you wanted to (which I have done, on systems where I don't have root or enough ownership to just throw things anywhere)
I always build SSH from source myself using my own scripts and meta-makefiles. Both the most recent OpenSSH release, and the latest one supported by HPN-SSH (for use on high-latency links).
OpenSSH 8.2p1 notably has support for using FIDO U2F 2FA keys to secure SSH keys, it works perfectly, as long as your server also runs 8.2p1 (only the client needs to be compiled with libFIDO2).
As for the Catalina train wreck, it's clear both hardware and software quality is on a severe downward trend at Apple, you can either rant and moan about it, or take control back by switching to Linux or BSD, which is what I am doing, very slowly and deliberately.
Never experienced this in a decade or so of using Homebrew's OpenSSH, but you can absolutely use something other than Homebrew to get a more up-to-date and standard OpenSSH install if you prefer.
