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I ended up figuring out the issue on mine, hopefully this helps others:

My target install machine is running Windows 7. According to a Windows guy I know, Microsoft changed the security API for a few different things going from Vista to 7, especially concerning a feature called UAC. UAC does not allow programs to write directly to the C: drive, so certain programs will not function properly.

One of these programs that fails (silently) is the WindRiver installer.

The solution? Log into an adminstrator account, go to Control Panel -> User Accounts and Family Safety -> User Account. Choose "User Account Control" settings (the infamous UAC). Slide the bar to the bottom, and restart your computer. You have now disabled UAC; you can enable it later (probably after build season).

Now for the fun part. Remove WindRiver entirely (i.e. blow away the C:\WindRiver directory). Pop in the WindRiver install DVD and run the setup program. It should install significantly faster. After that, run the update program on the same disk, then install the latest WPI updates. Once you've done that, everything should work properly.

Hope that helps!