Developement board

[mister_e]

Of course not the F877(a) as it's almost obsolete anyways. I would suggest the 16F887 or PIC18F4520... but that doesn't cover the USB. So go for the 18F2550 or 18F4550. As long as you can deal with the fact that the dedicated USB pins can't be used as standard i/o (mostly only as Input), then you should be able to cover almost everything you have on your current list...except the USB slave... where you need an interface in between OR go for a bigger PIC with USB OTG... but it won't work with PBP... nothing is perfect

PICKIT2 will be perfect... and now it has the Logic Analyser utility, that could be handy.

A bit pointless to go for the Bootloader... at least student won't learn how to set config fuses and how to program them in-circuit and how to design something for ICSP support. Pickit2 is a fast programmer, sure it's faster than most Bootloader.

Is there a board with everything in your list? Probably not 100%. Have a look at MikroElektronika EasyPic 5... and their expansion modules. And probably that one...
http://www.picbasic.co.uk/forum/showthread.php?t=8817

You could still design your own 'main board' on which you just plug some plug-in modules.

HTH