my family, and some of my friends are no woods-savvy...
my sister mostly through poor balance issues related to genetics, she has alot of trouble walking on anything besides pavement. my mom has never been too big into the woods, my dad and younger brother are both tech savvies that don't like to be without internet and cozy beds for an hour to two at most. my friends that don't hike are mostly ignorant about hiking, and wouldn't know where to start if i told them to come camping with me.
if i were going to try to go into the woods with a mixed group, i would advise driving somewhere and setting up a sort of base camp car camping style, with bug tent, inflatable beds, propane stove, etc. then from that take the whole group on long day hikes and expeditions one day, then everyone sleeps in base that night, then the woodsbums head out the next day for an overnight, returning the next day to basecamp. you can mix up the amounts of time that you split it up for (three nights in base, one night hiking/one night base, three nights hiking/etc)
just make sure while you are away hiking that the people that don't know what they are doing have plenty of firewood cut and split for them, so that they don't hurt themselves playing with the axe...and maybe hide all the sharp stuff just to be sure.
or just do two different trips, one for the sake of covering distance and enjoying the woods in a more connected way, another for the sake of bringing along extra steel and playing with new toys.