I stand corrected. But there still may be a way to make this work. I suggest you try programming the 18F2550 with LVP. Modify your home brew junebug/PICkit2 to pull the PGM pin to GND instead of using it as a bootloader button.(to cause it to run)
That should result in a working junebug (hi voltage programer) but without the bootloader switch on RB5.
You could then use the working programmer to program a 2nd 18F2550 using HVP and then swap it into the junebug and put the boot switch back.
I am not saying it will work for sure, I have been wrong once or twice
There are some notes in the datasheet that should be looked at. Somthing about the portb pullups, it may or may not apply.
3v0