If I am replacing the single coils on my strat with 2 humbuckers, do i have to get 4 conducter wiring humuckers or 2 conducter wiring to keep the 5 way switching?
It doesn't matter. The "extra" wires for a humbucker are for coil-splitting, and that type of thing. On the other hand, those are some nice options to have. But you don't have to.
I'd get the four conductor just incase you want to split. If you decide you don't, I'm pretty sure all you have to do is take the green and red (?I think, I don't remempber exactly?) and solder and/or tape them together.