That Kimberley Kamper is cool! Also, overland mom, good work on the decision.
I still have not moved towards a solution for us. Our issue is dogs. I love them and they are needy as all heck...GSDs evidently have separation anxiety, who knew. Anyway, I have my scout (SUV) and just got a tundra (truck). I point that out because the difference between truck and SUV can certainly affect your decision on sleeping arrangements. I'm planning on using the scout for shorter, warmer trips and it will likely be paired with regular ground tents or hammocks. The tundra, since it has storage space in the bed, will get a trailer. I'm thinking teardrop at this point. Too high of a tent and the pups can't get up in it. Shouldnt be an issue with a teardrop. And an adventure trailer would be redundant since I have the bed space. For an SUV ths thought process is certainly different.
Plus we are considering a move West where colder temps would make the hard-sided teardrop more useful for us.
I think given your circumstances the trailer with RTT was the most logical choice.