backwards you want the LEAST amount of surface area, less friction, less drag i don't know how else to put it. a single larger port will have less SURFACE area in the port than 2 medium size for instance
2 6's have about the same PORT area as a single 8
but a single 8 has less surface area in the port itself.
and for icweiner, they are not as light light or thing cardboard as you think, lots and lots of the home theatre guys will take a 18-24" sono tube and cut a baffle for either end and use the tube itself as an enclosure for their subwoofers, and i've seen mutiple sonotubes with big 18" drivers, IXL 18's, dayton titanic 15's... my point is they are beafier than you think but if you want the extra reasurance (i mean its just a port but suit yourself) you can take a little bit of fiberglass and reinforce the outside of it with a layer or 2 but i don't think its needed, its alot more solid than you think.
as far as flaring with a router here you go, its a system of a double baffle and flush bit and the biggest roundover bit you can find/use
http://www.subwoofer-builder.com/flares-10mm.htm
enjoy