2008 was an unusual election: even more than in 2004 there were decent grounds for libertarians and libertarian-minded people to vote for the Dmocratic candidate. Quite a few, including a good number of my friends, did so. Reason catches up with some of them here, asking if they regret* that vote.
For the most part: no, not really. The Buyer's Remorse was priced-in at the time of the election. True, the health care bill may be worse than some feared and true too there's been more intervention in the economy than libertarians might think either sensible or palatable. And, of course, Obama's record on civil liberties and related issues has been dismal.
But that wasn't the question in 2008. One thing few people have argued, even as Democrats prepare for a crushing defeat that will send them back to 2005-era levels of representation in Congress, is that everything would be better if only John McCain had won the Presidency. There'd have been a greater emphasis (proportionally speaking) on tax cuts but many of the bail-outs would have happened anyway (including, I suspect, the auto bail-out) and most of the arguments for the Tea Party would have applied to a McCain-led America too.
Nor, however much you may question many of Obama's decisions, can one think either Iraq or Afghanistan would have been better served by a President McCain - a man so severely lacking in judgement, remember, that his preferred choice for Vice-President was Joe freakin' Lieberman.
From a libertarian perspective, the Democrats have behaved as Democrats. This should not surprise nor, really, be worth complaining about. Anyway, Reason's feature offers a very fair (I think) appraisal of Obama's presidency so far.
*For what it's worth, were I an American citizen and had I voted I'd have voted for Obama in states where it mattered (ie, NH, PA, VA, OH etc) and for Bob Barr in states (TX, CA, NY etc) where it did not. I'd do the same today even knowing what we know now.