Replying in reverse order:
True, I enjoy the openness combined with conciceness / on topic habits, especially here at HN. My idea was not to reprint HN save as a cutaway box, maybe with 2d barcode links, to provide context for the written article that takes survey of, e.g. HN as a measure.
The value to the reader, is that by showing the original thoughts & debate, the reader can clearly see they are not receiving stale material, bounded by the three to six months print magazine lead time.
My editorial approach is to build ground up. Top down is the publishing (and programming) tradition: Plan, project, design, assign, assemble. But HackerDigest's approach i would be a clean slate, monthly: Follow discussions, cross reference trends, back check technical factors in the debates, especially not overlooking edge cases; compile overview; write synopsis; commission to journalists who can turn around fast, alongside seeking major vendor comment (something that would help drive advertising pitches) and publish.
I'd love to read your work, but I'm on mobile this holiday weekend so will probably have to wait until I'm home. However you seem to have simply stated how it can be hard, to become a paid writer, especially off your own bat.
That's a truism, I'm afraid. I've been frequently published, but under the unnamed title imprint (like The Economist, not yet unfortunately The Economist, a good school friend eventually strained at that limit with them, and his next told was surprisingly public. I don't know how hard it is to get good writers to forgo byline at least..but certainly that newspaper can.) Or as a ghost, more frequently for advertorials under a CxO's name.
I think my proximity to the profit centers in publishing, helps massively. I started in publishing, because in 1993, a fast growing stock market darling, had no sales who understood what multimedia was, so I got hired with almost a "start now" exhortation. I started next working day.
I say that, because -- at least in print -- I learned the financial constraints quickly (befriended by a ex PwC fellow who quit partner track off a first class math degree, because he rightly identified the optimization opportunity in print media, set against internet threat)
So I was first published when the pagination left space spare, and a advertiser who I had sold by comparing how their tech worked vs a forthcoming competitor ipo, and got their ceo to take the space if we could turn around advertorial fast enough to meet copy date. They already had display adverts, so this was the only thing that made sense.
As you know, highlighted even, possibly, by Medium, the economics of writing for online journals, is radically different.
Despite this, print has not - trade journal claims are misleading - fallen as significantly as you may believe. Traded forward, print ads in magazines, discounts to a $TLN market. I help super verticals,and trade association titles, discover sell side alpha. Why the trade press dismisses the print market, is a combination of traditional buy side monopolism, and the online advertising business lately being described by the outgoing CEO of Mediacom, as "criminal", no qualifications of that word.