1. All that was upheld was a single aspect – that a tax can be levied on people who don’t carry government approved insurance. They also threw out the part that states are required to expand Medicaid. The other aspects of the law weren’t involved and may be litigated later. If health care is not “interstate commerce” it isn’t clear how much of Obamacare will survive.
2. The Supreme Court seriously restricted the use of the Commerce Clause to expand federal control, which may throw many other aspects of “Obamacare” into question. They also seriously restricted federal mandates to the states, raising serious questions on many federal programs.
3. One can argue that Roberts managed to smile pleasantly while stabbing the liberals in the back. The approval of the Obamacare tax is hard to defend politically, can be changed easily in the future – and in return they lost much of their ability to regulate day to day life.
4. Given that Roberts is under 50, and has life tenure, he’ll probably be Chief Justice for the next 20 years, whereas Obama is likely to be an obscure professor trying to keep busy after next January (or January 2017 at the latest). Roberts really isn’t subject to much pressure.