The thing that pushed me over the Homebrew back when it was new was how with MacPorts, surprisingly often packages (at least those I was installing) were broken and required manual patching to make work.

While this would be a nuisance for me even today, I was only just starting to dip my toe into programming at that point which meant I lacked the technical knowledge to perform any changes more complicated than pasting in a single line somewhere, which meant it was often game over when a package was broken.

While Homebrew has its problems it’s easy to see how it became popular.