My grandfather worked on seismograph crews for an oil company after WWII. It wasn't long before they went with the crews from Texas to sites in Canada, Wyoming, and Montana. Money was slim and my grandparents hunted for daily food, even the early 50's. At some point they started camping out of a pickup and moved to trailers in the early 60s. My grandmother recorded all the costs for food, gas, supplies for all of those trips and I still have "The Book" that goes up to our last family trip in 1997. I was introduced to camping in 1976 as a two year old, in a hard side Mobile Scout. My grandfather passed away in 1988, so we didn't get to make a trip at all that year and soon after the Mobile Scout was sold because my grandmother had no interest in pulling it. Our next trip was in a tent for a week. We found that wasn't really something we wanted to pursue. A used Palomino Pinto pop-up was next. It didn't have more than beds, maybe a stove and a sink. I can't remember if it had a small ice box or not. We used that for two years before deciding to move up in the world. A winter trip to the RV show was planned for the purpose of looking at a new trailer to buy. We (I was still in high school) decided on a 1992 Jayco Cardinal SD. Sink, shower, toilet, refrigerator. A little convenience is always nice, right? We typically made full 14 day or more trips in the summer, so that convenience was welcomed. People started doing other things... my grandmother's sister and her family stopped going on our trips, mu uncle was not going anymore, my sister graduated high school in 1997 and I met a girl (who I would marry) in 1999. So, 1997 was our last trip in the popup. We did not sell it though, it was parked and something that just in the way on the driveway forever.
My grandmother passed away in 2014 and we started the process of deciding who was going to take what and what needed to be sold. I went back and forth for awhile, but decided I wanted to take the trailer. I repacked the bearings after sitting since 1997, bought some new tires and moved it to my place this Monday. My kids have been bugging me to go camping, so hopefully we can so something next summer. There is a lot of work that needs to be done before we can go.
I am not sure what I wish I had known before my first pop-up. We just kinda fell into it due to necessity. Years of camping were already water under the bridge, so we just had something new to sleep in. Along with that, I learned a lot from how they always did things. I don't have fancy wheel chocks or levelers or anything. I have a pile of 2x lumber that I pull up on to level and I have been known to go out in the bushes and find big rocks to use as wheel chocks. There have been times that a trailer corner was too high for the stabilizer jack to reach the ground and I have used a rock for that too.
We use a plastic gallon jug filled with water that we hang on a trip for a "sink". Punch a hole near the bottom and stick a golf tee in the hole as a "faucet". Put a bar of soap in a nylon knee high and tie that to the bottle. Nearly free easy handwashing station that I learned in cub scouts.
I doubt I will change much of the way we have always done things, the biggest challenge will be getting my wife and kids to do stuff the "right way".