For some reason I'd never seen Homebrew Cask before, which looks very interesting! Does anyone have experiences with Cask to share?
Cask could be awesome, but it's not at this stage. There are no upgrades, in many cases it doesn't work. Most apps complain that they are not in /Applications, but are in ~/Applications instead and so on. At the end of the day, it duplicates some of the Homebrew functionality - some non-GUI packages are getting into Cask, because possibly Homebrew doesn't want them - it's a bit confusing as well. I think efforts shou…
I'm going to address a few of your points specifically.
> There are no upgrades, in many cases it doesn't work.
It's true that `brew cask upgrade` is not yet a thing. I would very much like it to be. I've been sort of avoiding work on the feature for fear of messing it up. But that's no reason to not try to make something work! :) Maybe I'll use this as an occasion to start digging in and getting my hands dirty.
> At the end of the day, it duplicates some of the Homebrew functionality - some non-GUI packages are getting into Cask, because possibly Homebrew doesn't want them - it's a bit confusing as well.
If the purpose of the project is not clear, that's definitely a problem. I'm not aware of many (any?) purely non-gui apps making it in to Cask. The `Homebrew/homebrew-binary` tap is the place for those. I'll go review our included Casks to make sure things are clear.
> I think efforts should be put into merging into Homebrew instead of keeping it separate.
I can understand this opinion, but I think we may actually end up going in the other direction. The places we share code with Homebrew have been the biggest problem areas for us. We are already 90% code independent from Homebrew, and I think moving Cask to its own world may benefit both the project and the users. But of course that's a conversation to have with the (amazing!) project team.