I don't think that would make it much simpler (if that's what you're getting at). There's tons of grunt work that just has to be done - eg. calculating expected dividend payments (by automatically matching portfolio details to dividend schedules from corporate websites), and automatically matching those to bank account credits - all through code. Despite the laughs that the VB languages get on HN, VBScript is in fact, a fully featured traditional imperative programming language, and has all the features you'd expect in such a language (but no IDE :-(). So I doubt that rewriting in python would make much difference. And I'd still be bound to the IE automation model.