Our first camper was a pop up and we enjoyed it and made some great memories in it with our youngest daughter, but there are just too many compromises with pop ups. They lack security, they aren't comfortable in cold weather, they have a severe lack of storage space, and the components tend to be lower end relative to what we've got in our fifth wheel. Setting them up and tearing them down gets very tedious too, especially in poor weather. And any camping trip generally involved three different set-ups/tear-downs - one to pack and get ready, one at camp, and one after we got back home to clean up and empty the trailer.
Our fifth wheel is much more spacious, it pulls better (better TV), it's more comfortable, setup involves leveling it, dropping the rear stablizers and waiting 15 seconds for the slide to deploy. It also has far more storage space for our outdoor gear. I can see myself buying a bigger or smaller fifth wheel as needs change, but I don't see myself ever getting anything but a fifth wheel in the future.