It is cute that you pasted a lot of reference links mentioning css support. It would have been somewhat more effective if there were actual working examples occasionally. You certainly did not demonstrate that any of it would be easy...

kerning ... letter spacing -- It works "best" when pixels are used as the unit? Joke. Do you know the right amount of pixels for different line heights/font sizes? Calculating it every time is an easy implementation?

ligatures -- I could not find any good real world examples of @font-face, and none with examples of not inserting ligatures into words that should not have characters replaced by ligatures.

expansion/protrusion -- According to your reference NO MAJOR BROWSERS support it and the simple workaround is a kludge and does not work inside of flowed text. Joke.

wkhtmlpdf lists 50 something issues with fonts -- You don’t know what I am referring to? I am referring to the 50+ issues for wkhtmlpdf on their project. That is complicated?

negative letter spacing -- Letter spacing does not require a lot of effort with latex.

period after Dr. versus the end of a sentence -- You think manually specifying the behavior is easy?

frenchspacing -- You realize that your link has nothing to do with frenchspacing right?

babel/pollyglossia -- Yet again your link has nothing to do with the aforementioned packages.

Line breaking -- Do you really need a citation for html/css's awful line breaking behavior? Maybe this discussion is a bit out of your wheelhouse? To get html/css quality line breaks in latex you have to turn \sloppy on.

http://news.ycombinator.com/item?id=1974963 or http://web.archive.org/web/20070203140340/http://www.nat.vu....

bibtex -- What kind of question is the "ability to build a list of publications with bibtex in a resume/cv?" Vitally important for any academic field. (FYI by referencing I meant point your resume at a .bib file and having them seamlessly included) Have you tested this or do you have any examples of it playing nicely with all of the other hacks/kludges/might-work solutions you posted? What about changing the formats to a different industry standard? You think creating your own template to handle all the many corner cases is an easy solution compared to bibtex?

siunits -- Mathjax has nothing to do with siunits. Seriously this was almost as bad as your babel/pollyglossia solution.

page breaks? -- Awesome you found some css documents that mention page breaks and orphan control. Did you notice how widely supported this is? And how about these caveats:

"You cannot use this property on absolutely positioned elements.

Use the page-breaking properties as few times as possible and avoid page-breaking properties inside tables, floating elements, and block elements with borders."

headers/footers -- Should be? Lets try and discuss the things you know about and have a little experience with?

book quality publication -- I should have read this first. It seems that you do not really understand the requirements of publication quality documents. FYI, when you publish something most of the emphasis is on your consumer/audience. So while its wonderful that your prefer writing in markdown I am not sure why the consumer is going to care about your "syntactic perspective." Take a look at the highest voted answers for beautifully published documents:

http://tex.stackexchange.com/q/1319/7490

Or better yet try take a look at a tufte book and tell me that an html implementation would be perfectly fine.

wkthtmlpdf -- Its in the creator/producer field of your resume. You do understand your toolset right? You needed an additional tool to add metadata to your resume? You cant just add it easily by hand at the top of your document? Joke.