As long as there is no single prevalent native package format for Windows, packaging is going to suck on Windows. That's why this tool exists, but I don't think attacking a big mess with more complexity is the right approach. I hope I'm wrong, but I think this will end up 'successful' only in the way NuGet is 'successful' - there's not really any competition.
What I'd hoped for is that MS would commit to extending MSI to handle new use cases and provide actual good tools to make authoring MSI less painful. Maybe some kind of marketing or outreach to get ISVs to use MSI instead of the various alternatives. But for some reason they don't do that, and now it looks like one of the things cut to make Nano Server is Windows Installer (MSI), so I don't think it's going to happen.
Wait. Are you saying that MSFT is going to walk away from the everything-and-the-kitchen-sink installer format that is MSI? This is actually (seriously!) a bit surprising to me!
You probably have far more expertise in this area, but I don't see this as solid evidence that MSFT is walking away from MSI. I mean, they also removed WOW64 and the GUI.
It would be absurd to think that MSFT would ever drop support for the GUI in every version of Windows Server. :)
I don't, my earlier thoughts should indicate that I have less (or none). Thinking about this more it's more likely that Nano Server won't have packages at all: the container will be the package. You'll build the image and it will have whatever it has. If you need to add/remove 'packages' you will build a new image. So, no need for package management inside the container -> no need for MSI.
That's actually a really good thought about the reason for MSI removal in Nano Server!
(And, TBH, my only experience with MSI was briefly working with a vaguely recent version of InstallShield several years ago. The fact that you can talk about the pain of MSI authoring probably indicates that you understand more about the topic than I do. I just clicked some buttons in the InstallShield UI, and skimmed some of the MSI developer docs. :) )
What I'd hoped for is that MS would commit to extending MSI to handle new use cases and provide actual good tools to make authoring MSI less painful. Maybe some kind of marketing or outreach to get ISVs to use MSI instead of the various alternatives. But for some reason they don't do that, and now it looks like one of the things cut to make Nano Server is Windows Installer (MSI), so I don't think it's going to happen.