USRobotics had a much easier time with the original Pilot, the device that became the Palm. They just had to look at what Apple had done, take out most of the good features, whip something up on fugly hardware with way less electronics, cobble together a wimpy little OS and then release. It took them a long time to go from the original Pilot to where they are now. For many years the development was extremely slow going and in fact less changed in five or so years than from one generation of Newton to the next.
The only thing that surprised me years back was that Microsoft didn't come in and clean Palm's clock. But after seeing multiple iterations of Windows Mobile I knew that was likely never to happen. They just didn't get it. Losing all applications and data on your PDA because your battery runs out is not a good design choice. Pathetic products, including the latest. Generally there's no upgrade path for WinMo devices either. At least with Palm many customers had the chance to update their OS.