The always-insightful Matt Yglesias discusses the benefits and propriety of writing for free.
I would add that I see the new “writing for free” model as changing in (at least) two ways. First, high living costs make it harder to leverage the patronage of writers into significant impact. There will arise new arrangements where newbies are offered 15k a year to go blog from the Yucatan, or somewhere else with low living costs but ok broadband. Foundations or donors will pick up the bill and the newbies will consider the country to be an adventure not a burden. The “winners” of these tournaments will end up with jobs similar to Matt’s. Some people, especially those with “lender of first resort” parents, will manage to cover a Brooklyn lifestyle with the 15k.
Second, one’s choice of spouse will matter increasingly for journalism and also commentary. The returns to a good marriage will rise. Look for on-line writers to become slightly more establishment, slightly more romantic, and just a wee bit closer to the philosophy of Ross Douthat, minus the enthusiasm for a higher birth rate of course.