[Binome]

Well, if your into having usb connectivity and a nice selection of languges the microchip pic 18f2550/4550 series is pretty nice. They can run a USB bootloader, use minimal external components(a resonator and a couple of caps), and there are BASIC(picbasic/picbasic pro) and C(c18 student edition) compilers.

A good cheap programmer is the Pickit 2 from microchip, at around $35 its a steal for a high voltage programmer.

Now, if you have newer mac boxes, bootcamp might be your option because pretty much everything for pic development is windows only.