Tent and Jeep Grand Cherokee is how the wife and I started camping.
She got tired of the tent so we got a pop up tent trailer, still used the Jeep. Kept it 2 years.
I got tired of the hassle of the pop up so we stepped up to a 26' fifth wheel. Pulled it with a 2500 CTD. Kept it 2 years, was the biggest POS I've ever had, got tired of fixing it, so swapped it out after two years.
Traded up to a 32' 5er (our current rig). Lease ran out on the 2500, purchased a 3500 SRW short bed and pulled it with that for 8 years. When I upgraded the truck in 2011 I bought the 3500 DRW in my signature. Way too much truck for just my 5er, but I usually tow tandem.