I agree the "sympathetic media" angle rings quite hollow, and although I can't account for poor vetting by the Bush folks, team O can easily be scrutinized thusly...
They are as patient as they are ruthless. Whenever they dug up such dirt, by looking at sealed records, which clearly Bush didn't, they saw they could own him. Citizens United is small potatoes. That addressed money going into elections (which may or may not have been successful) for candidates who would support and vote for policy. Obama care is policy. It is direct control of 1/7th to 1/5th of the economy, depending on who ya ask. It is the cornerstone of Socialism and the basis for their buying power.
Heller? The 2d Amendment is attacked on every level anyway. Some jurisdictions will likely never submit, and they know it may come to a fight. I think incrementalism works better for them on that issue.
Are they that patient? To have sat on it for so long? If many reporters had it, some would not have had teh long view to do so, I think. It's possible that, for the narcissist's signature legislation, they pulled out all the stops and didn't have this until it was crunch-time. . They probably dug into every SCOTUS member who may have been wobbly or known to be the type to strike it down. As an aside, I wonder if this is about the time Boehner climbed into O's lap? He's been so compliant I can't help but think they got some dirt on him.
On the flip side, Robert's vote was hailed as a stroke of genius by Thomas Sowell, actually. An aspect I hadn't heard elsewhere. By calling it a tax, a revenue raising bill, it opened the door to more challenges on teh constitutionality b/c all revenue-raising bills must originate in the House, and O-care was a Senate bill!
Of course, G may be right in that Occam usually has the last word.