Wow. This sounds way too familiar. Our story is SO similar, even though there are some key differences. Started out with a smaller SUV, towing a popup. Wanted to upgrade from popup to small TT. Found that we would need a larger SUV to do so. Went and bought the larger SUV, then went looking at small trailers more seriously. The more we looked, the less we liked the smallest trailers. Found a somewhat larger (23', but still under 5000lb loaded) trailer and bought it. Towed it with our larger SUV (5000 lb capacity) for a year. Then decided that we'd be better off with a pickup.
The F150 super crew cab has MORE passenger space than our larger SUV. The back seat is enormous! The only thing is, it doesn't offer three rows of passenger seating.
I feel your frustration. I hope you find the best things for your family.
-Speak