Yes but I've never had a native tool fail on a missing libc. I've had several Python tools and JS tools fail on missing the right version of their interpreter. Even on the right interpreter version Python tools frequently shit the bed because they're so fragile.

I have. During system upgrades, usually along unsupported paths.

If you're ever living dangerously, bring along busybox-static. It might not be the best, but you'll thank yourself later.