The dilemma in supporting schools in using technology: Give out fish or teach to fish. Before I came back to school I was faced with this problem more than once.
What I would say now, in hindsight, is that if you make the solution yourself it adds risk. I thoroughly enjoy making simple scripts and workflows, but these are generally fragile. You might end up with more long term support than you thought, or worse raising and dashing expectations.
In my part-time life I am still supporting Glow Blogs. Quite often it would be easier to fix something in response to a request for help. More often now I try to write instructions instead. I can add these to the help and point the next problem a those.
I need to get back to microcasting. I enjoyed listen to this on my commute. The focus on one subject in the short form podcast is valuable.