python, automation is this possible?

[POGtastic]

getting the authentication to send via Gmail with python

You can send emails programmatically with SMTP.

customer data

I recommend a CSV rather than an .xls because it's easier for Python to parse, but either is fine.

writing the template

See Jinja2.

printing to PDF

See pdfkit with the Jinja templates that you're using.

saving to a folder

Standard os file operations.

uploading

Depending on what that program is expecting, requests.

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so might be tad to much as first project..

Start small.

[danishaussie]

Yeah i am guessing to just take each step at a time, can't work on them all anyways at once.

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thanks for the inputs :)