[diebeforei485]

It probably would work fine, except that you'd be paying US cost of living (healthcare, rent, etc) while not on a US salary, so there doesn't seem to be a point - you're most likely burning money doing this and if you're hoping for a path to legalization, the issue is Congress can remain irrational longer than you can remain solvent.

A lot of people do what you say, but for a few months at a time (within the terms of their visa), every 3-4 years. During those months you could maybe get rent a Manhattan apartment (on airbnb or something) and experience living in New York, visit national parks or other attractions, do some shopping, and after a few months (6 months is the legal limit I think) you've probably experienced most of what you need to know.