I've recently had to make an installer for application that I wrote for my job, and it sucked. I used the Qt Installer Framework, and I had to hack together the option to overwrite an existing installation. The kicker is that it seems I was the first person to solve this problem and post a workaround for it on the internet. This is the same installer framework the Qt framework uses mind you... I never want to deal with this again.
I have looked at other installer solutions, and they all seem so complicated. Yes, a lot of the time people in the handmade community can just throw around zips and call it a day, but non-developers expect installers, and I often need to produce one.
What do you guys use to make installers for Windows? I've looked at what needs to happen in terms of the registry, and it doesn't seem as complicated as the internet makes it out to be. If I can't find a reasonable one, I will probably be writing Handmade Installer. I'd also like to hear about what you guys are doing for things that go along with installation, like signing executables.