Given Trump’s authoritarian tendencies, it is virtually a given that he will attempt to stretch his legal powers to the maximum extent possible. When that happens, the first line of defense will be the federal judiciary.
You can expect to see plenty of litigation filed in District Courts in blue states. Many of the judges in these areas will be Obama appointees, and Trump cannot fire them. The outcomes will depend on the facts and the legal issues, of course, but in general, I would anticipate that Trump’s won/loss record won’t be very good.
How will the man on golf cart react to adverse court orders? Will he obey or ignore them? Based on his behavior relative to the judiciary to date, it’s hard to be very optimistic on this point.