I have considered a quilt, and a tarp (to kind of answer both of your questions). I am so far a bit of a chicken, with these types of things. while the concept seems sound, the implentation of these "seems" more difficult to me. For instance, i have read over and over again, that pitching a tarp CORRECTLY so that it keeps you dry takes practice and experience. Neither of which I currently have. I was thinking that the tent, along with its bug protection, may be a beter first step for me. The quilt is similar, so to speak, although I think its more user friendly.
The wife picked up a neo air at a REI garage sale but the son and I don have pads yet. I am leaning in the direction of a foam pad, but sleep is important to me, so I may take some extra weight for some comfort in this area. I actually plan on just going ahead and buying a zrest or similar and trying it for a night in the backyard...I mean for 35.00 how bad can it be even if I decide I dont like it for the long term.
As to the family buying into all the aspects you listed, I think so far we are all OK with the issues. Of course thinking this, and knowing it by having done it, are two different things, but we are active outdoor persons, and so far the cold or hot hasnt bothered us much. The wife is not thrilled with the no shower for days part, but other than that, no major fusses.
The boy has to come, he doesnt have a choice...I know, I know, mean parents, but this is our family time together, and this is what we all agreed we are going to do. On top of that I suspect years later, he will be glad he got to do all these trips and see the sites we have seen. I see so many folks who live here in reno who never set foot off a paved road.