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.
I don't think you need to go from Sinatra to Rails - I actually started with Rails and like dhh said - before I knew it I was building real apps. Rails provided a great framework to get something up and running. It provides MVC and interacts with a database. After familiarising myself with Rails I started using Sinatra (which doesn't offer any MVC or support you get from Rails) and then ultimately started coding just in Ruby. I don't think there's any issue with the learning curve for Rails because it provides the support where you need it. I speak to new developers all the time who use Rails and get it almost instantly - releasing apps a week or two later.
Thats what I was thinking... rather than translating from scratch perhaps put it out to Mechanical Turk or another automated translator, than refine manually using your expertise?
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."