Timing doesn't work for Obama. He'll be 55 when he leaves office and he'll want to decompress, write a book, and make some money. HRC would rather appoint someone in their late 40s/early 50s. Even if Dems control the Senate, they won't have 60 votes. Someone like Cruz or Sessions could still filibuster his nomination. Didn't think it was possible, but Hillary could be treated worse than Obama. With Trump in the race, Hillary may put up a bigger electoral college total than Obama, but she'll win with less than a majority of the popular vote.
Summon the Feelings Police, we have a Code Six Persecution Complex in progress...