Optimizing for HN frontpage is a terrible idea. (1) HN users are usually hostile against titles that even remotely look clickbait and flag them, (2) It attracts the wrong audience to the blog post.
It always depends on what you want out of it. Some people are outcome-oriented. They want reputation and/or the affirmation of crowds, and for them, writing is a process of reverse-engineering what people want to read. At a deep level, they don't want to write, they want to have written something popular.
Others are journey-oriented. They write to work ideas out. paulg championed this o̶v̶e̶r̶ ̶a̶ ̶d̶e̶c̶a̶d̶e̶ ̶a̶g̶o̶ almost twenty years ago when he wrote an essay explaining that the word "essay" is not just a noun, but also a verb suggesting an attempt or experiment: http://www.paulgraham.com/essay.html.
For some ideas, trying to explain them forces us to confront the idea cheaply and identify areas where we haven't thought things through all the way.
And of course, sometimes it's a little of column A, a little of column B. Speaking for myself, my taste is almost entirely for column B: http://braythwayt.com/posterous/2014/10/30/write.html. But this is a big world, and if someone wants what's in column A or to sprinkle some column A on their column B essay, well, this post provides some hints.
But of course you need to contribute things back or you will get negative score and banned, so I mix in some things I know will get upvoted as well.
"Good headline writing" to me suggests being attractive to people who will like the contents, but also allowing people who might not care for the contents to self-filter.