In my last test, I tried WSI with w0rdpress 2.3.2 and 2.0.11. In both cases I could get blogs to install, but none of the options were set correctly by wsi. In fact, even the template rotator would fail to use any template, resulting in a blank page. I could still go to the admin page of each install and set the plugins, template, options, etc, so at the very least the install is copied to each location for me. I wouldn't exactly call that a time saver, but its better than nothing.
Perhaps the software hasn't been updated since wp 1.5 or something like that, which is why I also tried wp 2.0.11, the earliest build I could conveniently find.
Another note, wsi also failed to install correctly in add-on domains, it only worked on domain accounts. I haven't tried it on sub-domains, but at this point I'll probably dump it and look for another mass installer. any suggestions as to which one works on wp 2.3.2??