So my bands trying to get some shows going on and we're not entirely sure how to go about backed tracked keyboards live.. I thought perhaps recording them and having the drummer start them via computer and play along in time? HELP!!
that's pretty much it, but your drummer is gonna need a metronome track, to keep things in the correct tempo... so you are always gonna be limited in that sense, no speeding up, or slowing down during songs (unless you do a specific metronome track for thar)
how would i go about having both play (the click track and the keybaords) but the click going to his headphones and the keyboards on the PA?
The easiest way is to have the keyboards panned hard left and the click track hard right. Then it's just a matter of using a splitter cable to send the signals where you need them to go.

Simple, but it works.