I'm curious: how is Homebrew a kludge? Also, the *BSD userland command-line tools on macOS aren't old, they are fairly close to the latest updates for bash, git, vim, etc.
Homebrew seems far behind dpkg/apt in terms of managing complex dependencies and versioning. It's gotten better, but largely by replicating the complexity of those systems.
Last I looked unzip on MacOS still couldn't handle files > 2GB in size. That was a patch submitted about 10 years ago. The version of less is also ancient and compiled without standard features like LESSKEY. At least as of a year or two ago, it's been awhile since I've tried using MacOS.
