Let me preface this with that I don't know a lot about Wilson.
I know he was a segregationist and was quoted in the introduction to Birth of a Nation, and that certainly doesn't endear me to him. But what I like about him is that I associate him with the high tide of progressivism (the income tax amendment; the FTC, the Clayton Antitrust Act, child labor laws, and yes even the Federal Reserve). I think the US entry into WWI, while not entirely necessarily, was not heinous either, may have helped to shorten the war and more than anything else pushed the US into superpower status. And while he failed to get the US into the League of Nations or negotiate a more sustainable Treaty of Versailles, I blame the latter on British and French vindictiveness and the former on his opponents in the Senate. I think the League of Nations overall as a concept was vindicated by the UN.
I do wonder why people keep blaming or praising Wilson for the 16th Amendment. It was sent to the States under Taft. 34 of the necessary 36 States ratified the amendment before Wilson was even the Democratic nominee. All three major candidates in 1912 were in support of the 16th amendment. After the election was over another 6 or 7 states ratified the amendment before Wilson took office (Massachusetts ratified on Inauguration Day, and I don't know if they did so before or after noon.)
Granted, Wilson was a major force behind the passage of the Revenue Act of 1913, but the income tax levied in that act was incidental to the reform of the tariff.