Looks certainly doable, but I doubt there is a class or template that yields your results without some manual work on getting the formatting right. I'd use LuaLaTeX (because there are underlined things, and underlining text is a hard problem in TeX without LuaTeX, for which there is the fabulous `lua-ul` package). There are different projects to generate HTML from TeX, some of which look quite promising, but I have no experience with any of those.
But I have to say, that PDF has a very non-uniform look to it :) Nothing I'd personally want to create. Also for someone not that experienced with TeX it might be a good idea to use a different method to generate something like that (for instance, with a quick glance I spotted nothing that couldn't be done in Markdown).
