After despairing of ever solving this yesterday (and for the past 6 months really), I've got the webapp running on Windows with no visible DOS box. Also have the assistant starting up in the background on login.

It turns out a service was not the way to do. There is a way to write a VB Script that runs a "DOS" command in a hidden window, and this is what I used. Amazing how hard it was to work this out, probably partly because I don't have the Windows vocabulary to know what to look for.