In 2020-2021 I participated in the Building Beauty Online course (the architecture side) and the Beautiful Software seminar. I wrote up as much as I could:
Basically dump everything in ~/Downloads and then a couple of scripts to archive it off to ~/doc/YYYY-MM every month, then every now and then I might sort that into ~/archive/home/doc and ~/archive/work/doc.
Got a few context-specific directories; ~/src, ~/screenshots, ~/notes.
Like you said, I get people to use Sinatra for a while before getting in to Rails. It gets them in to MVC style apps while keeping things simple. Definitely recommend it as a stepping stone to Rails.
They're probably (almost definitely) both automated emails. The point is that they're a bit better than "Hi. Click this link. Buy some more stuff from us."