Campers 101

[earplug]

Much depends on your time and wife. We went from motorcycle, car to pickup camping to popup then she quit. If you only get out for a day or so the hassle of a popup can get old. They eat propane when its cold and windy.
If you have a flat bed trailer, I'd consider a slide in pick up camper, then you won't be stuck on paying two trailer tags and the hassle of two sets of tires etc. I have seen neighbors go from Popup to 18 foot hard side to 25 foot and then buying a F-250.
Do you have friends that camp? If the kids have other kids to play with all is better. Dogs in camp grounds are a hassle.

[Great-Kazoo]

Dogs in camp grounds are a hassle.

Almost as much as a wife who doesn't like camping but, wanted to make you happy.