Since I crossed over to the Ubuntu side, I’ve fallen in love with the debian repo system. However, I still need to create Windows installers, primitive and sad as they now feel :-)
I’ve been using the Visual Studio Setup & Deployment projects for ages. They’re pretty damn inflexible, but solid, and the integration into the build is a lovely thing. Great for in-house deployment. However, they’re seriously limited, and you can only build them using the dev environment, albeit from the command line, which means you need to install Visual Studio on the build server.
A solid open source msi creator would be awesome. I think I’m at the point where I’d be willing to put in the time to learn something a little arcane, if it gives me more control. The tool for the job looks like NSIS. There’s even a gui for it.