I have a feeling, over the course of the next few months Obama will come out and give a few anti-Trump speeches over things like Obamacare, they will get a ton of glowing press coverage, but elicit little more than a yawn from Congress and not change the political dynamic any. Then as the media realizes he is not the savior they need, they will quickly turn their sites on other potential 2020 democrat candidates to lead the party, and once Obama realizes he isn't getting the media love he craves, he will slink back into obscurity to write his memoirs...
Trump is going to get so much done in the first 100 days that people are going to be wondering what the heck has Obama been doing these past 8 years? He had eight years to give us the "hope and change" he promised and he squandered them badly. But see, Obama never actually had a real job in the real world so he never had a work ethic and almost all his hires were done for political and patronage purposes. Basically a bunch of incompetent flunkies.
Donald Trump works pretty much from 4am to 10pm every day and hires people that are competent and even more importantly holds them accountable. Remember that he went through three campaign managers in the recent campaign. This was portrayed by the media as a sign of a "disorganized campaign in chaos" when it was actually Donald Trump being not afraid of making command decisions on the fly in order to reach his objectives. This is how an tried and true effective businessman operates.
The first 100 days of the Trump presidency will be a thing of beauty and by the time Obama returns to DC from his "Palm Springs vacation", he'll be totally irrelevant to the Democrat Party and they will be looking for new leadership to take them into the 2018 and 2020 campaigns. Maybe they will choose leaders who have actually accomplished something in their lives.