As you've already seen, Matthew's working on making Docvert as easy to install as possible. For what it's worth, I've been setting up server-based OpenOffice converters for years, and usually the tricky parts come down to a few areas:
- OpenOffice seems to work best when installed on a Linux/Unix system, and the more recent/supported, the better
- if you can get GUI access to the machine, even over VNC, it makes troubleshooting much easier
- take your time with user permissions, and check them carefully (especially root/admin permissions)
I have successfully installed OpenOffice and Docvert on a number of platforms, through innumerable hoops: Mac OSX, various flavours of Linux (RHEL, Ubuntu, Debian), via X11, VNC, and headless using xvfb. I've never tried on a Windows machine, so I couldn't say whether it'd be easier or harder. If you're going to take the latest Docvert 3.4 out for a spin, I'd love to hear comments on your experience so we can share them with others who are looking to do the same.