Earlier today (minutes ago, in fact) I wrote a post discussing the challenge posed to the Left by the civil-liberties-affirming Right. In short: when out of power, it was very, very easy for the Democrats to get the votes of those against the police state. When in power, they have to not only stop expanding but actively dismantle police state apparatus (Patriot Act, I'm looking at you) in order to not be the police state party.
There are inherent political challenges in this at any given time: alienating security conservatives, tarnishing the records of prominent Democrats complicit during the Bush years, potentially finding ones hands tied in acting on new information. There are new and exciting challenges that one can add on to this: trying to end it while aiming for National Reconciliation, the very identity of the President making him more prone to crazy domestic violence, and trying to extinguish state power in one arena while expanding it, in, say, the area of healthcare.
The key to expanding the state in one area while retracting it in another is, as I see it, about the framing of rights. The police state violates very clearly defined freedoms: it takes away privacy, autonomy, and presumed innocence. Ending the police state means guaranteeing those freedoms.
Healthcare has to be framed the same. Currently, healthcare means uncertainty, high costs, employment-dependence, and inefficiency. It does not mean, as the most adamant free marketeers will tell you, than procuring health services is a matter of choice and desire. When you need healthcare, you absolutely need it. No amount of bargaining or negotiating or price-comparison will help. Healthcare is a terrible good to have rationed exclusively by the market - it creates a surplus of cosmetic surgeries in the same nation that has 1 in 6 uninsured. So framing the current system as the free market is an impossibility.
Instead, Obama's healthcare plan, and all other universalistic healthcare programs, need to frame the very program as a freedom: freedom from risk, freedom from uncertainty, freedom from impossible costs, freedom to transition between jobs while still being insured. This isn't the state stepping in and forcing a program on people; this is the state removing unfair burdens and affirming the inherent freedom to life.
If people see healthcare as a freedom and not as a government program, and if police state programs are repealed, I think the Obama coalition can last for at least another decade. More importantly, it will both fulfil campaign promises, and give the Left an opportunity to stop being the "big government" party and instead become a political party about freedoms.