Can't argue that Obama care isn't a form of payroll tax, as it clearly is. But having watched the vote take place regarding passing Obama Care, especially in the Senate, I have no doubt whatsoever that a single payee system such as we have in Canada was never a viable option. There simply wasn't enough votes to pass this type of bill. That aside, I'm sure it was his first choice but for better or worse reality got in the way.
I also think he could have done more in terms of removing the Bush cuts and regulating the financial industry, but that said, I don't think the blame lies squarely with him. With the polarization of US politics one can only imagine how many Tea Partiers there'd be in Congress now had he eliminated the Bush tax cuts, in the middle of a recession no less.
I personally think this recession has hamstrung him to a great extent, and while I basically agree with you regarding corporate bail outs, I do think GM and AIG really had to be bailed out, and I'm sure if they could have done it again they would have bailed out Lehman Brothers.
Essentially all were too big to fail.
As for Chrysler, it too probably needed bailing out as well, as the whole support industry in the auto sector would have collapsed, and since much of the vehicle production is outsourced, it could very well have taken Ford down with it. But philosophically I don't think anyone was overly keen on having to go down this path, it just happened to be the best out of a bunch of lousy options to chose from. (ie the least worst option)