I don't think you'll see too many disagreements here, especially regarding MSI. I think one thing to keep in mind is to watch the way many programs are using MSI files these days. Displaying UI dialogs and making complex configuration choices with an MSI is very weak simply due to the way Windows Installer was designed, so I've noticed a lot of programs being split into a bunch of baby MSIs that are installed with the minimal UI by a parent setup program. The SQL Server 2008 setup wizard does this. UPS WorldShip does this. And Paint.NET does this, too--the wizard you see is a Windows Forms app, and it launches msiexec
itself (you can see the minimal UI of the Windows Installer pop up on top of the white wizard window), passing any configuration parameters as property arguments to msiexec
.
A common scenario where this comes up is where someone is tasked with building an installer for an application that has both server and client counterparts. If the user chooses the server option, then they may or may not want a new database to be installed, which means installing SQL Server. But you can't just install SQL Server while you're in the middle of your own installation because Windows Installer won't let you do that. So a frequent solution is to write an app that displays a wizard that allows the user to configure all of the setup options, and then your app launches the MSI files as needed for SQL Server, your server application, and your client application in the minimal UI mode; basically, eschewing the "features" aspect of Windows Installer entirely and moving it up to the MSI level. 4.5's multiple-package installations seems to be a step further in this direction. This format is also especially useful if you also need to loop in non-MSI installers from third parties as part of your installation process, like installing a printer driver for some bizarre point of sale printer.
I'll also agree that Windows Installer lacks built-in support for common deployment scenarios. It's meant for when setup isn't XCOPY, but they seem to miss the fact that setup usually isn't just "files + shortcuts + registry keys," either. There are no built-in actions for setting up IIS Web sites, registering certificates, creating and updating databases, adding assemblies to the GAC, and so on. I guess they take the opinion that some of this should happen on first run rather than being a transactional part of the install. The freely available tooling and documentation has been awful--flat out awful--for the better part of a decade. Both of these issues are largely addressed by the WiX project and DTF (which lets you finally use managed code custom actions), which is why we're all so grateful to Rob Mensching and others' work on that project.
I've had the same experience. Installation can quickly suck up your time as you go down the rabbit hole of "Oh God, I guess I have to become an expert in this too." I second the idea that's it's best to address it early on in your project and keep it maintained as part of your build process. This way, you can help avoid that scenario of having developed a practically uninstallable product. (Trac was an example of this for a while, requiring to track down specific versions of weird Python libraries.)
(I could go on about how Windows Installer sometimes decides to use my slow, external USB hard drive as a place to decompress its files, how it seems to sit there doing nothing for minutes on end on computers that have had lots of MSI installs on them, and how that progress bar resetting itself a bazillion times during a single install is the most idiotic thing I have ever seen, but I'll save those rants for another day. =)
My two cents; please note that I really just know enough about Windows Installer to do damage, but this is my assessment coming from a small business developer just trying to use it. Good luck!