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I recently went down this path. I discovered the WiX MSI toolkit and it was very smooth. If you ever find yourself needing to create an installer and haven’t used it, give it a look. It can install dependencies, customize the UI, create/start/stop/remove Windows services, configure IIS websites, and run custom actions.

It’s all done via declarative XML and made my life much easier.

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WiX is great tool but a bit steep learning curve because it won't abstract MSI spec so I need to learn MSI spec.

It is powerful, but the curve is really steep, and it is still subject to the seemingly random, myriad of constraints and limitations - for example, there is a whole class of variables that you can only write to at certain stages in the install process.

The last MSI installer I wrote had to install 2 Windows services, write to the registry, grant file system access rights, and install a minifilter driver. There was a lot of swearing, and I was really close to launching my laptop out of a Window several times. It was a very unhappy period of my life, and if I never have to write another MSI installer, it will be too soon.

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