XC Trip with 12yo - TT or PUP? WWYD?

I've had popups for many years. I quickly learned to not go camping if rain was predicted. It is a tent and even if rain doesn't get blown inside by the wind you can't put it up wet the next morning or it will mildew in warm weather. I had a brand new one really torn up by an unpredicted sustained high wind and rain overnight. The canvas is like a big sail and all the rocking was scary enough to keep us awake. We were wet and miserable. The dealer was kind enough to give me a good deal on replacement canvas but the support poles were floppy from then on. I still own one and like camping in a pup but personally I wouldn't consider an extended trip in one. I've also camped in just a pickup camper shell with the wife and 2 kids when they were young. Wasn't that bad just crowded. Made a twin size bed that fit sideways over the bed rails. The kids slept underneath that which left room in the back for our gear, even a port-a-potty with privacy curtains for #1 use at night. Rainproof, lockable, and no hitching or setup time, which can really get old quick if you're not staying long in one spot. I like the "plug and play" experience you get with a pickup camper or motorhome. Plus no backing up a trailer which requires some skill if you get blocked in at a gas station or fast food joint.