Yes, the repression will stop, and it is insulting to call the Obama administration the worst in US history. How has Obama failed. He helped get the country out of a recession and has made it safer to be a minority in the United States. He will be truly missed.
Someone has to have judged it the worst after some historical perspective, which hasn't happened yet. I'm not sure what you mean by "Repression" but if you're talking about the press, everyday there are negative articles about the President, so it's not being censored. This isn't Russia, so journalists aren't being imprisoned for writing critical pieces.
It is no longer a recession. It is permanent economic decline because of the choices of policies in the United States over the last 100 years. The United States has decimated what used to be the most free economy in the world. Now, there are rules and regulations. Business cannot cope with these rules, so the economy has permanently fallen apart.
Unfortunately, much of the repression taking place in the United States today will not stop after the Obama Administration leaves. This is because the electorate that gave us the Obama Administration will likely be voting for Hillary Clinton. Much of the electorate has become dependent on government for power and money. Therefore, working Americans and small businesses will continue to be repressed.