In a sense, we had a similar RV journey. In 2009 we traded in our Coleman Popup for a Rockwood Roo 19. After 7.5 yrs, we decided we were getting too old to lift the bunk ends, so we traded up to a KZ Connect; I think it was a 231BH. I liked the floorplan, but I HATED towing that trailer! It was too big and too long!
It didn't take long before we realized we needed a newer tow vehicle but what we really we missed was hearing the sounds of nature, so we traded the Connect for a new Rockwood Roo, this time a 183. This works out great because my niece usually travels with us, so everyone has a bed to keep all their stuff with them!