The problem that I face is that I don't get $20/mo of value out of any one publication (ok, I guess NYT is $17 per 4 weeks, which is a bizarre billing cycle). I certainly get (more than) $20/mo of value out of "online news" as a whole, but it's spread out, and any given site would probably only get a few dollars a month (and many sub-$1) if allocated what I'd consider fairly. But pretty much no news website will let me subscribe for that little, or will give me a cheap plan that limits me to, say, 10 or 12 articles per month (which would still be overkill for many of the paid sites I'll occasionally click through to).
If I were to subscribe to every site where I've bypassed a paywall even once in the last few months (of have just given up without reading), I'd easily be spending over $300 per month. I don't feel like my consumption warrants that price.