The Senate Parliamentarian, Alan Frumin, will be the one who, if necessary, will decide which aspects of Obamacare are legitimately relevant to the budget process, and therefore eligible for passage by the reconciliation process, which only requires 51 votes to pass rather than 60. Frumin has wide latitude in interpreting the Byrd rule: "A provision shall be considered extraneous if it produces changes in outlays or revenues which are merely incidental to the non-budgetary components of the provision."
He can be fired by the majority party; his predecessor was fired by the Republicans for ruling against them too often, including one ruling that only one tax bill per year could go through reconciliation, and another that stopped the Republicans from using the reconciliation process to end all federal funding for abortions, which the parliamentarian interpreted to be social rather than fiscal policy. But firing him just for blocking health reform would be overkill, unless his rulings were really over the line.
Both parties seem to like Frumin. He is willing to help people write legislative language so that it passes muster.
So he was hired by Republicans (potentially bad for Obama) who wanted someone who prefers broader use of the reconciliation process (potentially good for Obama). Highly speculative tea-leaf reading.
Obama just needs to write his bills carefully. They're probably working on it already. It really shouldn't be hard to show that passing a multi-billion-dollar health care program is a legitimate budget issue, provided that Frumin doesn't take the hardline position that it contains too much social policy -- which isn't really in the spirit of the Byrd Rule anyway. And of course the Democrats can probably ask Frumin for help in editing the text.
Of course if Obama can round up 60 votes to bypass the Byrd Rule, Frumin doesn't have to do anything -- Obama wins.