John,
It sounds like a great project, but recognize that "doing it right" is going to be a lot of work. A 3-way, 5-driver speaker is not for the faint of heart. Perhaps that's why no one has chimed in yet.
I think to get responses from the gurus that frequent this forum, you'll need to take it as far as you can and then ask specific questions. Start with XoverPro and see what sort of response you get... post the sims and ask for tips on fine-tuning.
I'll try to help along the way, but there are others with much more experience on this sort of thing than I. I'd start with 300/3500 1st order and see how it models. When you're in the final tweaking stage, my Schlumberger response analyzer (actually borrowed from work) and measurement mic might come in handy.
Incidentally, were you thinking WMTMW, WWMTM, side-firing woofers, or some other variation? With woofers mounted near the bottom, a tapered (pyramidal?) shape might help reduce diffraction and raise the baffle step compensation frequency. On the other hand, Dynaudio, Dunlavy, Focal/JM lab, and others have used the WMTMW approach to good effect.
Finally, are you going to tantalize us with some of your spectatular 3-d renderings before you fire up the table saw?
