Everyone that supports Obama and his ideas is most likely a socialist. I don't really think he is pretending to be a socialist, he just is a socialist and everyone knows that. Most democrats are socialists since they believe in big government which leads to socialism. So yes I would say Obama is a socialist.
First, the idea of Socialism is the exact opposite of Liberalism. It's true that, even though both parties in the USA are liberals, the democrats (which are the ones who usually receive this label) tend to have policies with socially aware approach that makes them closer to some social democrat principles (which by the way weren't at all supported by Lenin, as someone here claims). However, democrats are still liberal, and Obama is a textbook example of the democrat ideology. Obamacare, for example, even though often attacked as a socialist policy, is far from being so. Socialists would advocate for universal health care provided directly by the state, while Obamacere maintains the USA as one one of the only countries on the planet where there is no type health care provided by the state, and is therefore in compliance with the liberal principles dominant in that country's political arena.
One public policy a socialist leader does not make. Just because Obama legislated ONE policy that happens to coincide with Socialism doesn't make him a socialist. He may be liberal, but he isn't all the way to the left.
Secondly, I doubt democratic Socialism would work, because that is what Lenin wanted, and that never actually happened. Their elections are rigged all the time anyways.
Democratic socialism is the form of socialism enforced by democratic majority vote instead of statist authority. This means that the poor are provided for and the people have a say. Please check out subjects before you say stuff. Random word filler here: All my people talking all this stuff about me, why don't they just let me live?