You have 3 questions. 1. I have used Fink. And I have used MacPorts. Now I use Homebrew. 2. When I get super-annoyed with a system, perhaps because it has e

You have 3 questions. 1. I have used Fink. And I have used MacPorts. Now I use Homebrew. 2. When I get super-annoyed with a system, perhaps because it has entered a state where it won't update, I do a web search to see if folks have jumped from that ship to another. If there is a consensus, I jump with crowd. If not, I try to clear the decks, e.g. reinstalling from scratch, to see if I can improve my situation. 3. I don't have a list for you on the pros and cons. There may be some merit in choosing a system that is widely used, because then others might be able to help you if you encounter problems. By that measure, I think Homebrew is the best choice at the moment. But I've no reason to think there won't be something else just around the corner. I wish Apple would get in this game, but after so many decades of Apple standing by without acting, I am not especially sanguine.