Everytime I power cycle my amiga, I have to power cycle the plipbox first or I can't communicate with it.  Is this normal?  It won't work ever if I do a soft reset.  I have to physically power off the amiga, power cycle the plipbox, and then turn on the amiga.
yep its normal.
I power my amiga and plipbox off the same psu,so switch on/off takes care of it. u could prob. add a momentary power switch to the plip if thats not a option.