The biggest issue the Democratic party faces in general is the fact that most major news media is owned by folks who would be just as happy to live under a GOP-forever regime if the Democrats aren't equally positive on pro-big-business issues (like punishing immigrants to keep wages down)

IMHO the biggest thing we need to do as progressives is find better ways to wrest some control of the messaging away from billionaires. Even under the Reagan administration the GOP was much more neutral on immigration, the fact that we are collectively not is a deliberate propaganda strategy IMHO.