When comparing Fink vs Homebrew Cask, the Slant community recommends Homebrew Cask for most people. In the question“What are the best Mac package managers?” Homebrew Cask is ranked 2nd while Fink is ranked 8th. The most important reason people chose Homebrew Cask is:
Homebrew Cask adds functionality to Homebrew such as allowing downloads of commercial licensed apps.
Specs
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Pros
Pro Will be familiar to apt-get users
Fink is based on apt-get making the transition to anyone used to Debian-based environments easier.
Pro Install from source
Pro Packages provided as binaries
Installed applications don't need to be compiled and built on the system.
Pro Extends Homebrew
Homebrew Cask adds functionality to Homebrew such as allowing downloads of commercial licensed apps.
Pro "Zap" application configuration
this is an interesting feature allowing user to remove application configuration leftowers
Pro Manage graphical applications through the command line
Homebrew Cask allows you to install graphical applications through the command line, rather than having to go through the standard installation process.
E.g. brew cask install google-chrome
Cons
Con Doesn't support newer macOS versions
Doesn't support macOS Big Sur or Monterey. Says it's "coming soon."
Con Pre-compiled packages are often out of date
It happens often that the user will come across out of date, pre-compiled packages. This can impede on using new features released in apps due to using older releases.
Con Cask update is usually manual
This defeats the purpose of the packet manager.
Con Requires Xcode
Homebrew Cask requires that Xcode is installed, which may be more work than what some want to spend on configuring this app.
Con Software no longer needed by anything (orphans) is hard to delete
Con The developers are hostile to the users reporting issues
Con Silently spies on the user by default
See here.
Con Duplicate apps found in brew may cause issue
There are warnings provided that apps found in brew should not be installed with brew cask (and vice versa). While the user is warned of this, mistakes can happen, which would be better to just see them avoided all together by not supplying duplicate apps.