Hard to say how complicated this will be without knowing your system, and what the passive crossover does.
@erik_squires - My system is described on my Main System virtual system page, but to elaborate a bit more - my speaker system is a dipole line array with Bohlender-Graebener NEO10 midrange drivers, and NEO3 tweeters, with dipole woofer towers, each using four 12" servo woofers.
The BG drivers have a fairly smooth response, so the crossover is fairly simple - 12 db/octave LC filter for both NEO10 and NEO3 driver arrays, with an additional LC notch filter on the NEO10s. The woofers are driven by Rythmik plate amps that have their own active crossover (along with a simple parametric equalizer).
I don't think it will be hard to set up a DSP to do the same thing, although I'd probably use a 4th order crossover since it's fairly simple to do with DSP and makes it easier to get a smooth phase response.
The NEO line arrays are fairly efficient at about 98db/w. I'm currently driving them (using the passive crossover) with a 300B PSET amp (monoblocks). With an active crossover, I'd probably continue to use this amp on the NEO10s and build another SET amp for the tweeters.
I may be able to bypass the crossover on the Rythmik amps when using the dsp. If not, I'll set it to it's maximum crossover frequency and work around it with the dsp.
I currently use REW with a calibrated UMIK-1 mike. I suspect this will be adequate to set up the active crossover, but I'm open to suggestions.