The high pass (to your main amp) is typically applied before the sub's amp. However, the high pass is still another device between the preamp and main amp, so you're dependent on it's quality (although it's just a capacitor, but how good?.) Further, you will have four cable connections between you preamp and main amp instead of two, plus some internal wiring (in the sub) of unknown origin.
If your preamp has two pairs of "main outs", and depending on your main speakers (you didn't say) the ideal way IMO is to run them full range from one set of preamp outs, and run the sub (again, you didn't say what kind) from the other set of preamp outs, just enough to fill in the very bottom that your main speakers miss.
If your preamp has two pairs of "main outs", and depending on your main speakers (you didn't say) the ideal way IMO is to run them full range from one set of preamp outs, and run the sub (again, you didn't say what kind) from the other set of preamp outs, just enough to fill in the very bottom that your main speakers miss.