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As a security measure, the Terminal does not display anything as you type, not even asterisks (*). If you get some kind of error, it might be because the Admin account doesn't have a password set. Installing Homebrew should only take a few seconds or minutes (depending on the speed of your internet connection).
Plus, Wine is open source, which means people are continually improving it and adding new features. A lot of people discover Wine because they have one specific Windows program that they need to use, and it's the last thing preventing them from switching to a different operating system. The short answer is: probably, but it's worth checking.
The Wine project maintains a database called the App DB that has user reviews of how well specific Windows programs work under Wine. (If it's not listed, that doesn't necessarily mean that it won't work — only that you're apparently trying to use a very obscure program!
) To install Wine on your Mac, you will need the following: To check what version of mac OS you're running, click on the Apple logo on the far left side of the toolbar, select "About This Mac", and look at your version number under the big "mac OS" or "OS X". You need an Admin account on your Mac because only Admins can install software.
Homebrew is a package manager that makes installing open source programs much easier.
In particular, trying to install a large program like Wine without the help of a package manager would be tremendously difficult.