YWFFTMMR

Presumably, on backchannels we're not seeing, he's getting contacted with those "offers" that he is complaining about now that he's having some success, all involving the "proposition" he describes. The problem is that Dave has been around for decades now, still occasionally talks about how Apple "locked him in a trunk" a long time ago, and basically has the wisdom to avoid this problem now, having learned the hard way. He loved the Internet at least in part because he saw it as the platform vendor that could not lock you out. (Sort of a virtual platform vendor.) This is far from the first time he's made this complaint, so at this point it seems he's pretty justified in calling this a pattern.

Many people have many different opinions of Dave Winer, and these opinions are frequently not without some justification, but two points should be remembered: He really has been around a long time and has experiences that should be considered (in particular, if he's saying something is a trap I'm inclined to take it seriously), and he is a doer, that is, one who does things, not just talks about doing things. (If he taught me anything, I would say it was "Stop talking and start doing", which has served me well.) His implementations aren't always the best technically, but they do things. He didn't invent the idea of XML-based newsfeeds, but he is basically the guy who built the tools to make it happen in an open manner. (Which is why I could claim a couple of days ago that I've been reading RSS feeds for nearly ten years; it will be ten years next January. I was reading RSS when it was only Dave's software that could generate and consume it.)

So, that's the current backstory, to the best of my knowledge. No guarantees it is complete or correct, but I tried.

No.

A slight overestimation of his importance to the Twitter ecosystem.

Self-Important (adj): see: Winer, Scoble, Arrington, et. al.

But I am also confused as to what exactly he's talking about.

The internet is based around people doing things for free for the good of the larger internet community .... While I can't tell for sure, it seems this person is unhappy with giving out his insights for free to the public.

The author, Dave Winer, helped invent RSS and personally invented OPML, so he has no problem with giving out his insights for free to the public and helping the internet community. In fact he says as much in the article: "I figure if I'm not going to make any money off my work, then I'll work in an environment where no one does." This is an allusion to standards and open source work (though I guess if you're not familiar with the author, that wouldn't necessarily be clear).

What he's talking about is when businesses approach him to work for free while they're planning to make boatloads of money from that work. From the article: "People don't work for free. They don't pour out their passion in the cause of making you wealthy."