Andrew Sullivan was one of the first I remember who put up a Tip Jar and he's done okay, but he finally moved on to associate with a legacy media outfit in Time. Whether that's becuase the tip jar dried up or his tastes changed I don't know.
I finally broke down on Friday and dropped some coin in Michael Totten's box (not much, but about what I'd shell out for a higher-end magazine subscription) because I decided I'd gotten enough value out of it to merit payment. He's posted several times a week, if not every day, for just about the entire time he's been overseas, only taking "breaks" when he's off doing real work. There's no comparison between what he does and what the pajama-clad masses do.
Today, coincidentally, Michael's post explores the possibility of doing more of this kind of work if the money keeps coming in, as it's proven relatively profitable. He sees it as the beginning, maybe, of a real shift in the business model of the media. I'm not sure of that, though some of the most exceptional writers may be able to carve out a niche like Michael's.
So, what would you be willing to pay for?