Regarding Obamacare — if your income is below the federal poverty line (FPL- $11,490 for an individual), you aren’t eligible for subsidies on the exchanges, because you qualify for Medicaid. That is, unless you live in a state that has not expanded Medicaid. Then you’re probably just screwed.
However, according to this article — if you overestimate what you actually think you will earn in 2014 so that you can get the subsidy you won’t be penalized for it later. In some cases the subsidies can cover the entire cost of the insurance. So if you know anybody who might be in this boat, give them this tip.