Will the Democrats look back and wish McCain had won?

It's a reasonable question, given the direction things are going. Obama has been a disappointment in many ways, and what's worse the nation has lurched seriously to the Right in response to lack of success in generating a strong economic recovery and his unpopular healthcare plan (which, ironically, is probably the most right-wing way of doing universal healthcare possible, originally devised by Republicans and first instituted by Republican presidential hopeful Mitt Romney). Now that the House is controlled by Republicans again, and crazy ones at that who are threatening to let the country go into default if their demands aren't met, which means no further stimulus is possible. The already totally inadequate recovery is sputtering, which means there's a very serious possibility that Republicans will sweep the 2012 elections--assuming Obama can't ride their delusional decision to push Paul Ryan's abolish-Medicare-and-replace-it-with-Obamacare plan all the way to reelection. It also assumes they don't give themselves another serious self-inflicted wound, such as nominated a lunatic (hello, Michele Bachman) and the Tea Party doesn't run it's own candidate (if, for example, Romney gets it, which Republican nomination history suggests he will).

There's a serious argument that McCain, hamstrung by a heavily Democratic congress, would have been the better way to go. Assuming he didn't do anything nuts, and didn't drop dead leaving Sarah Palin in charge, the practical results probably wouldn't have been that different from what we've actually gotten from Obama. We wouldn't have Obamacare, but that's quite unpopular anyway and might end up being repealed in 2013 before it is fully implemented. Also, the bad economy would have reinforced the Bush legacy and might have led to 20 years of Democratic hegemony, as happened during the Great Depression. Instead, it's putting the same people who caused the collapse back in power.

This isn't the first time that Democrats have won an election they'd have been better off losing. I doubt any liberal thinks their cause was advanced by Jimmy Carter winning the White House. Quite the opposite, dramatically so in fact. One can even make the argument that liberalism would have been better off if George H.W. Bush had gotten a second term (heck, the fact that it would've made George W. Bush much less likely to be president alone makes that idea very attractive).