I'm going to go with the fact that you're a white guy with dreads that made the border guards want to give you additional scrutiny. It had nothing to do with your story or vehicle.
How did you cross the Colombian jungle ?
I drove a much less ambitious route from Colorado to El Salvador and, of course, thought about continuing to go south ... but all accounts led me to believe that it was essentially impossible to drive continuously through Colombia ...
Looks like I've seen some of your videos on YouTube before, when looking at videos about people who live out of their Jeeps. However if money wasn't a limit I probably would want a class A RV, but the Jeep Wrangler makes a prefect tow car, people in the RV community call them toads. But you leave your RV at a camp spot and then can go explore in the Jeep, grocery shopping, etc without needing to break camp.
But yeah I think the nomad lifestyle has its challenges, but also some great things too. I love going to new places, reminds me of family road trips back when we used to go somewhere every year.
I quit my job and spent 2 years driving from AK to Argentina, then again to spend 3 years driving around Africa. I'm now a full-time nomad, and doing everything I can to never sit at a desk again (freelance writing, photography, published books, etc.)
I certainly get some good interactions at "first world" borders, but nothing really bad. When I drove into the US on my way to Argentina it was obvious the officer simply didn't believe I was going to drive into Mexico. Even with the map on my hood [1].
Recently I drove into the US with my passport full of visas from 35 different African countries (even Sudan, Congo, Nigeria, etc.). The border guard flipped through it and said "Wait, WHAT do you do?".. utterly confused. I told the whole story, showed him the new map on my hood and again he was just confused. Friendly, but confused.
I was detained once at the border coming in by bus from Canada... the border guard was not convinced I was not going to stay. After 5 hours they let me speak and I mentioned I had a ticket out of the country (flying out of LAX like a week later).. when I showed the ticket the officer said "Where's Sydney?"
It's all good.
[1] https://www.instagram.com/p/ByyD2J_lfmE/ [2] https://www.instagram.com/p/Bw4h0X_Fq_G/