@Noah Gray - I love your energy to explore flying with the family!!!. Often flying isn't for the "whole" family. So don't be discouraged or give up if one or two of them just don't like it. You never know it might just end up being you and your wife or just you and a kid.
So I was going to ask. What is the longest trip you have done as a family so far? That might give us a better idea of where you are at w/r to the family comfort zone and your experience already.
For example, if work wasn't taking up our time my wife and I would hop in the old Skylane and fly all around the country. My daughter would be "no thank you Dad".
However, I just got her scuba and nitrox certified in Key Largo in August. If we were based down there, she would have already pestered me to no end to hop over to the Bahamas. But the wife isn't a water person and would be rather nervous on that and I could see here sitting it out...the first time