I should also add that while I think Obama was a fairly decent President, and that he achieved some noteworthy things, "working on the margins" with "executive power" is an inevitable failure. The moment Trump takes office, the American government will be rolled back to 2010.
In other words, the only way to achieve meaningful and lasting change is through the legislature. When the Democrats had the legislature, they blew their entire mandate on a healthcare system whose main benefit is to fail and be replaced by a much better healthcare system (single payer).
I am firmly convinced that the only way the Democrats will ever be successful in making necessary changes is if they largely abandon establishment and defeatist politics. We all saw what Obama did when he campaigned on a platform of hope and change. I also think we are all now aware that people are more desperate for change than they are a cohesive policy agenda. Democrats need to take these lessons to heart and stop electing supposedly "sensible" moderates whose single greatest accomplishment has been getting Trump elected into office, losing control over most States, losing the Supreme Court and losing the House and Senate.
That means taking risks. No offense to guys like Kane, Spider and Dylan, but the best thing Democrats can do is stop listening to them. Republicans have learned that when you define the boundaries of acceptable political discourse, you control the conversation. I'm not sure when leftist politics became so heartless and cowardly, but there it is. You either aim big with the chance of losing, or you aim small and are guaranteed losing.