When I started camping I used a tent. Carried it on my motorbike and travelled everywhere.
It was natural that when I started taking my family camping, we'd use tents and we moved from the fast-setup 4-man dome tent (I can get one up in a couple of minutes) to a double-dome 14-person tent for the wife & I, with the main room used for eating, refrigerator, battery, chairs & table - for 4 people - the daughters used their own tents (personal choice).
Rain was a problem in setting up and pulling down, it's horrid to have all that wet material around, but it's do-able. Biggest problem is the setup/pulldown time. What should have taken minutes to achieve ended up taking hours, with the gazebo, folding tables, extra tarps etc etc. I ended up hating it.
So we bought a small caravan. Superb. It was so good that when the caravan started to fall apart, we were eager to find another and we ended up with the double-axle van that we have now.
Even if it were a small pop-up camper it would have been an improvement over what we had, and I know that you can buy these second-hand for a couple of thousand - do the little bit of work that's needed and off you go. All-weather, minimal setup time, increased carrying capacity compared to tents, easy to tow.
It depends on how hard you're wanting to do it. You can get big vans into difficult places if you are careful enough, so little pop-up campers are a breeze. For something truly hard like the CSR, towing anything at all is not recommended and a roof-top tent is the way to go, but a normal tent that doesn't take forever to set up would be more than satisfactory.
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