I'll miss him. Operations wise he was far from the most prudent, strategic planning anyone? However, his contributions to DPR are large. The Cruise Ships, HKDL, Cars Land, and Aulani were all started under him.
They've had an a profound impact on the way DPR were operated. He also looked at expansion beyond the berm as critical to the longterm success of DPR. He launched MyMagic+ which is another unique take on expansion in the theme parks beyond just building more.
That's perhaps his legacy. For him, traditional WDW was looked at as a burning platform. Attempts to fix it were all about keeping guests on property in the WDW ecosystem. This strategy has found great success, while also irritating the heck out of certain fans. Much of the major DVC expansion happened under his watch too. He reshaped WDW as a Resort destination with theme parks instead of theme parks with resorts.
He was radical in his thinking on building urban entertainment centers, DVC away from the parks, hotels in major cities, and apparently even character dining establishments were explored in major urban areas. Sadly most of those radical projects never played out.
That's not to say he didn't have issues. While I personally believe that he eventually would've seen the light, his New Fantasyland plans were less than stellar omitting even the mine train. Pathetic really. He was incredibly slow to build new rides in the parks (besides HKDL and DCA) because of his pursuit of construction outside the parks. To cap it all off, DVC by many is looked at as a negative and the hotel/resort focus is seen as a distraction from what really matters. Theme park operations. Let's also not overlook the fact that WDW quality got progressivly worse through his tenure, and have gotten better under Staggs.
So while many of his projects eventually got WDW back on track, he also missed opportunities. His focus on outside the parks led to some of the finest Cruise Ships in the world, while also stealing focus from the bread and butter of the business. His focus on MyMagic+ and keeping guests on property have changed the way many vacation for the better, and many of the biggest fans for the worse. He wasn't the best, but he was willing to take risks.
Though Staggs has won the day, I just hope he stays focused on the parks.