As a kid, canvas tents, then the parents found the money for a popup, then after a few years, they got a well used 21' Winnebago that would sleep all 6 of us.
After I got out on my own, back to tents, but the fancy nylon ones with a rain fly. Then up to a Cabelas Alaskan Guide 8 person tent. Still have it, but haven't used it in years. Then up to an 8' popup TC, then the 11.5' S&S TC that we still have, but it was WAY too much for my F-250. It is now an apartment at my parents on the other side of the state. Because of the S&S, we bought the 28' Arctic Fox 5er we have now.
I still have a 3 person backpacking tent for the motorcycles, but DW has never slept in it. I still enjoy it at least once a year.
I was also one of the snobs that turned my nose up at trailers, until the DW said she was tired of sleeping on the ground nearing 50. That was the first TC, and I saw the light. It really nice to have a bathroom a few steps away in the middle of the night, and be able to look outside when it is raining.