Well, the family connection/support issues prevent us from car-free status as well. My folks live far enough out of town that a quick run to do chores (several horses) and whatnot is not feasible by bicycle. Nor is hauling large loads of horse doo for composting and 3 grandkids for visiting very easy on two wheels. Thus, I have my subaru outback and a trailer my dad got me made out of an old pickup bed.
I consider myself car-lite instead of car-free. I figure with as few miles as I put on my car, it will last me a lifetime and I'll be one of those grannies with an old car in preemo condition.
So, I guess the long answer is that I'm not much help for addressing your question.
The reality of my and perhaps our situation is that we are situated in a car-centric culture and everything is designed around it.
Moreover, at least in my case, the dedication to bike-centrism is relatively new, thus our family of 5 is not 100% "on board" so to speak, let alone the expectations of extended family. I expect it will take many years to complete the transition. In fact, unless I move closer to or much further from my folks, I may not ever be able to be completely car-free. That's just my cultural and situational reality.
However, I am working very hard to show my sons how they can be perfectly mobile w/o a car so that as they start making their lifetime committments and plans, they can see there is a way to reduce their dependencies on personal motor vehicle ownership.