I hope it's not too late to weigh in on this.
Way back when I worked for the state of Texas, I was asked to generate something like 45 emails a week to managers around the state, each one of which was an HTML form that was essentially a sophisticated time sheet for their employees. Managers were to verify/correct and then send them back. I asked for a server (could have used an already existing SAS server - all generation and processing was done using SAS), but was denied. So I was forced to do all this through my email (Outlook) account. Originally Outlook would allow me to batch send these, but when we updated, the Outlook api/server required a manual verification of every batch to be sent. This was in place for some 2 1/2 years and survived 2 or 3 audits (with dings). Only mentioning this because even given a python, or any other script, you might be blocked from mass emailing by the server.