Wilhelm II was viewed by many of the German population as an ineffective and weak leader, one of the harbingers of the downfall of the German reich.

He lived his latter days in exile in the aftermath of World War I, and his reign was a major inciting factor in how the Nazi Party managed to seize control so effectively - Wilhelm was a major propaganda piece, and the Nazis promised a return from the downfall of what Wilhelm brought upon Germany, from a disastrous war to the Treaty of Versailles and the crippling of Germany's economy.

This was somewhat exacerbated in terms of propaganda by Wilhelm's deposition of Otto von Bismarck. The German people in the Weimar Republic idolized Bismarck and Germany's second reich during his reign. Bismarck eventually resigned over continual leadership disagreements with Wilhelm, which was viewed by many Germans in the Weimar Republic as the beginning death knell for Germany's proud stance and heritage. Thus, in the Nazis' promise for a return to Germany's greatness during the second reich under Bismarck, they effectively embraced the already omnipresent distaste for the events of the past few decades under Wilhelm II to seize control.

In regards to Hitler: Wilhelm was "proud" of him in the sense that he admired his accomplishments, particularly in the beginnings of World War II, and sought to use Hitler and the Nazis as a platform to return to power (or at least the restoration of a monarchy). Hitler, of course, did not feel the same, and Wilhelm's sparse attempts at communication with the ruling party failed.

Sources:

The Coming of the Third Reich, Richard J. Evans, Penguin Publishing

The Third Reich at War, Richard J. Evans, Penguin Publishing

The Last Kaiser: The Life of Wilhelm II, Giles MacDonogh, St. Martin's Griffin