For me it was easy. Dad was military and we traveled a lot. Enjoyed seeing the country and had to try to see it again from an adult's perspective, thus the campers my wife and I owned.
I brought my kids to Disneyworld in an Astro, which made sense financially at the time but really made me wish I had a popup. The next year I bought a cheap 8' box popup from a rental place, they were buying new ones. $1800 for that. Quickly determined we needed a bit more space with the two girls. $3500 for a Coleman Utah with the kitchen slide out. The kids had a blast, even though we only camped 2-3 times a year for the 4 years we had it. It was in good shape and we sold it 4 years later for almost what we paid for it originally.
We took the kids out to Niagara Falls one year. They won't forget that, they still tell me how cool that was, even the negative parts with my truck broken down in Wisconsin in very high heat. We used 12v fans to keep cool.
So was it worth it? Absolutely. It brought our family closer together.
We settled down in a seasonal campground 7 years ago and my grandson (he's 8 now) loves coming down to see us. We had squirtgun fights and he swam in the pool, "drove" our golf cart, had smores over a campfire and got to ride in the ATV. All in 2 days.
For grins, maybe consider renting a small popup for a weekend and taking it on a trip. Nothing special, but it could help you decide.
