I haven't read the entire thread so this may have been mentioned already, but you may try renting a pop up for a few weekends this summer to see how you really like it.
I've been camping since I was 5 or 6 (I'm 37 now) when my parent bought their first camper (a pop up). They progressed up to finally getting a travel trailer just before I moved out.
After my wife and I got married, we went a few times with my parents in their travel trailer, then we bought a tent. After an outing or two with that (my wife hated the tent!

), we bought our first camper, a Jayco pop up. It had a roof A/C that did really well keeping it cool in the humid summers here in MO. We used a ceramic heater for heat and it did an acceptable job. After a few years of the pop up, we upgraded to a travel trailer. After 7 years of that and after adding 2 more kids, we upgraded to our current camper, a 32' fifth wheel. Since we have 3 kids, this gives us all plenty of room to enjoy ourselves when it's raining, or too hot or cold to be outside. No, it's not roughing it, but it's enjoyable and allows us to enjoy the outdoors without resorting to sleeping on the ground or using the woods as the bathroom!