I recently purchased the book "The Definitive Guide to Windows Installer". I haven't really started reading it yet, but the source code and sample files are available online so I starting testing the sample .msi files in wine and windows out of curiousity . These files are relatively small and are targeted to demonstrate specific .msi functionality. They might work nicely for testing installer functionality in wine without being obscured by large amounts of other application related debug output.
http://www.apress.com/book/downloadfile/1645
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