> I have only a B.S., negative net worth, and no special skills except web dev (which is increasingly worthless these days). Are there other avenues to emigration that I'm missing?

The TN visa works in both directions - you can go work/live in Canada or Mexico. A BS is plenty; I'm not sure that "web dev" is a valid category, but you can probably find a job in either country that does qualify. And if it doesn't work out, you're just a quick plane ride home.