I use a similar workflow for my resume (really it's just a hand-written html file with some css templates for different section types), but I haven't found "printing to PDF" to be adequate. All the common browsers override your stylesheet with a "printing friendly" one, and do things like putting the URL at the bottom of the page. Instead, I use wkhtmltopdf instead, which is entirely adequate for this purpose.
I have an invoice generation script that outputs html, and I unfortunately have to open it in Chrome and "print to pdf" manually. If you control styling, you can usually set it to look the way you want. Also browser HTML headers/footers can be disabled.
wkhtmltopdf output never looked quite right to me.
