"Overland" style trailer - who has(had) one? Advice?

I used to have a M101 military trailer that I converted to 12 volt, electric brakes and a lighter 3500 lb dexter axle that matched the bolt pattern on my jeep. It was a good setup and I used it as a utility trailer as well. Unfortunately the jeep burned and I didn't have anything to tow it with. I ended up selling but it was a nice setup. Use a ground tent now.
 

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My buddy has a Fleetwood evolution e3 pop up camper and he tows that thing into some pretty rough spots all over NV. They’re decently priced used and most have a large outdoor storage deck in the front for coolers, dirt bike, bicycles etc. He’s had his 6 years and it’s held up. I’ve thought of buying one too. Pic is just a random one I found online.
 

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I used to have a M101 military trailer that I converted to 12 volt, electric brakes and a lighter 3500 lb dexter axle that matched the bolt pattern on my jeep. It was a good setup and I used it as a utility trailer as well. Unfortunately the jeep burned and I didn't have anything to tow it with. I ended up selling but it was a nice setup. Use a ground tent now.

Always thought those trailers were cool and have thought of kitting one out.

In 1953 George and Joy Adamson took a similar rig from Nairobi, across the Sahara, to Dover England. More than 5500 miles.

Joy.jpg
 
One thing to think about with roof top tents and setup and tear down- theres still a ton of setup tear down to fold everything back together with the cube style that fold in half

If you go with a more expensive, hardshell wedge style, those unlatch and pop up with gas struts. very quick setup/tear down. Getting gear/bedding in and out will take longer.

I have a Gofast superlite, no gas struts or latches, so I unzip and set in a couple of poles. Very quick setup, couples minutes at most.

The ladder is a bit annoying.
 
Reading your posts in seems like you are more concerned about fuel than anything else. If that is the case no matter what direction you go, you are not going to be happy because of fuel. Another choice is spending your funds on another crewcab pickup with 8' box and build an overland rig.
I am concerned about fuel for sure, and if my fuel economy went from 20mpg to 8-10mpg yeah that's no bueno... but a 3-4mpg loss for ease of setup would be worth it.

As far as building a true overlanding rig(i.e. RTT on vehicle, bed built out for overlanding) for my use it would be inconvenient at best. We typically drop a base camp somewhere and move around from there. While I guess base camp could be wherever we end up for the night, sometimes places get busy and camp spots fill up especially on weekends... so in that context, a true overlanding rig wouldn't really be ideal.
 
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