I would suggest Microchip's PIC18F series. I just started developing for them with the RealICE in-circuit emulator, but the pickit2 is a decent debugger for the price. You could say this for the AVR's also, but there is a large following for the device all over the web. I was able to have a - buggy, yet functional - embedded USB device running within days due to all the PIC related chatter.
The only thing I don't like about the PICs is that a lot of the sample code is VERY entwined into the demo boards. That can make it hard to tear out sections that you need and still have an application that will build and run for your application.