For our family of 6, we have moved from tents to a popup to a hybrid travel trailer.
The tents didn't work out well at all, as my wife was never a fan of them, and so for many years, we didn't camp. In 2009 I bought a huge popup camper from a co-worker (1996 Coleman Cheyenne) for $2k. In the next 5 years we took it out sporadically, but still didn't camp much as a family, but then we were having babies every two years or so. I still took the older boys out on scout trips with the tents.
In 2015, with our youngest now 3, I told my wife I wanted to take more adventures, and for spring break we scheduled and took a 3000 mile trip with the popup that stretched from Cincinnati to Kansas City, south to Dallas, then on to Waco and San Antonio and east to Lafayette LA, and then we headed north and home. We met up with a ton of friends on our trip and loved it. This, coupled with our yearly trip to Florida to a time share I inherited, taught us that we liked doing road trips as a family, but that we didn't like the 45 minutes to an hour of setup and tear down with the popup, and pulling a ton of stuff out onto a picnic bench during each one. Especially when we were also moving every day or every other day. Also, living out of a cooler for a week at a time wasn't the best either for 6 of us. More coolers would just take up more space. The popup didn't have a fridge, but a vertical icebox cooler that you had to set up the camper to get into, so we didn't even use it. We also lost the cover to the AC unit on the way from Dallas to Waco.
After that trip, we looked at a few travel trailers, just window shopping, and almost purchased one, but ultimately decided to just keep rolling with the popup. We were having some issues with the plastic exterior of the camper deteriorating, plus the floor really had some soft spots forming from leaks or just rot. I put a huge fiberglass patch on one corner due to the roofing cracking.
Father's day weekend that year, we took a 1000 mile trip to Washington DC. We had a great time, except when a storm rolled through and pounded the camper for about 6 hours. We stayed dry, but were stuck in the camper that whole time. There was a camper store near the camp ground, and after a day of exploring the DC mall and museums, we stopped and looked around and dreamed about what would work better for our family. I was really leaning towards a hybrid, as it was smaller, and we could park it in our driveway, and still gave us tents to sleep under. My wife wanted a bathroom, as during the pouring rain, it was very difficult to dash the 300 yards to the campground bathhouse. On the way home, we had a catastrophic tire failure. Thankfully I had a spare, and it only stopped us for about 25 minutes to change it, but it was the final straw..
We started looking at campers every weekend. And after about a month of looking, in July we decided to purchase a 2016 Jayco X23B hybrid. We've taken a few short trips (Indianapolis, Big Bone Lick State Park, two trips to Columbus) and we have taken three long trips (Disney Camp Wilderness, another DC trip, and one I will get to in a moment). We have found some issues, but overall, it works for us. We also upgraded my wife's vehicle to make towing better for all of us. We used to use my 2006 Land Rover LR3 for towing, and did use that for 3 of the small trips, and one of the large trips, but we sold our 2006 Odyssey minivan (spit) to some friends, and purchased a 2013 Dodge Durango. It gives us everything we need during the week, and a decent platform for highway miles and for towing the hybrid.
We just got back from a 10 day, 2000 mile trip of the Carolina Coast this past weekend. We headed south on good Friday, and spent the night just west of Ashville, NC. Setup takes about 20 minutes, 30 if I really take my time. Saturday, we tore down and got on the road and headed for Charleston SC. Set up again, and had a relaxing dinner. After a huge breakfast we left camp Sunday morning and drove to Patriots Point and spent the day climbing on an Air Craft Carrier, Submarine, and a destroyer from WWII, and took a boat ride to Fort Sumter. The next day, we packed up and headed up the coast to New Burn, NC. We spent two nights there as well, and checked out the Governor's Palace (Tryon Palace), and the associated museum, and also just walked around downtown New Bern (also the birth place of Pepsi Cola). Packed up there and headed to the Outer Banks. Dropped the camper off, and drove the 50 miles round trip to see the Wright brothers monument. Would have liked to spend more time here, and really would have liked to have my Rover for that area with all the off road areas. Future trip maybe. Next we headed north towards Williamsburg VA. We had planned to just keep driving, but it took us 6 hours to get from the Outer Banks to Williamsburg, and we decided to just spend the night and explore there, and then head home the next day. Friday the 21st, I backed the camper into the driveway around 11PM.
Our definition of overlanding is a bit different than most of what you see on this site, but it works for us, and we actually get out and explore now.
Since that first big trip in 2015, we have visited 20 states. We have plans for at least 2 more this year, and possibly 6 more next year.