The basic idea is everyone has different goals, ideas of what is fun or not, or as has been mentioned -is what your definition of comfort is, or put another way do you want to rough it or just kick back, eat good, be warm and enjoy that beer and watch the world go by from your nice comfortable chair in the high desert. Since you surf and hike now, you are already learning what you need to know to survive to be able to enjoy the next trip out. I'm 80 now, and I have spent most of those years working (the BLM (retired), and playing (camping, hiking, car and truck camping , backpacking) in the back county and throw in a hitch in the Army and I still am alive and kicking. I am probably more lucky than smart to make it this long, and hope for a few more years to play! What I took from all that -situational awareness- never ever do anything without understanding about what you are planning to do first and, just in case, if things go wrong, being prepared for whatever happens-both good and bad!
Getting a pop-up just increases the opportunities for more fun and trouble. If you break down out there in the back country or break your leg or run into that grizzly bear that wants to eat you or what ever, what you have with you in both experience and gear will determine whether you come back or not. As you get older (or wiser), all these things you carry change. When I retired and bought my Four Wheel pop-up--- boy did my ideas change. After 20 years of having my pop-up, I don't need all that survival and off road stuff I used to carry because I do different things for fun now- but what I do carry will hopefully get me out. Less gear, more fun stuff (maps, & more maps, a GPS and lot's of books to read) but if that fails and I need help, a Spot 10 to call and have someone to come a get me (it costs me $ but that is okay by me)! Use this site (and others like it) for help, lots of good info here-for example, a few months ago we had a great discussion here on whether or not you should get a hot water heater-check it out
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! Is it a must or something you can live without. I talked to much-have fun learning to enjoy life,
Smoke