There is a nugget of wisdom from Ragman. Be honest with yourself!
Will you really pull a trailer on a more rugged off road path? Trailering off road is challenging and your stuff will "shift" as it bounces around. Compartmentalized storage will aid with keeping things in one place. Weight is the enemy most always, and will be hard on the tow vehicle going slow up steep 4x4 trails. Factor in the weight of WATER and where it will be carried when traveling. "Stuff" adds up when packing.....generator, wheel chocks/blocks, grill, firewood, extra water, some kind of potty and potty shelter, solar suitcases, cords, fuel for the generator........all bulky at the least, and likely heavy. Will you pull mostly from point A to point B (so take the trailer with you) or will you mostly pull out to a basecamp?
It's ALL choices, and ALL involves compromises. I'd suggest designing to the 85% or 90% use level and not the last 10 or 15% level that you THINK you MIGHT want to do. It's that last 10 to 15% that gets expensive. In our minds eye we are going to trailer up Mount Everest and enjoy a 5 course gourmet dinner up there. I'd suggest that you might not go quite that far, LOL.
It's a great idea to rent one and use it locally just to try it on for size so to speak. You will quickly identify several things that you like or don't like when really using it vs. looking at professional photos online.
So, we already have all the gear we'd need only currently it all gets loaded in/on the truck which is then putting the truck pretty much right at RAWR and FAWR. We have no plans to take a generator, we would be using solar. At most we might pick up a small inverter generator in case of emergency on a longer trip where we expect to be out in the middle of nowhere for multiple days.
I've also already towed a much larger, heavier travel trailer (5,000LB loaded, 8.5' wide, 10.5' tall, aerodynamics of a brick) up, over, and down places like the Beartooth Pass (10,900ft) outside Yellowstone, Wolf Creek Pass (10,800ft), etc. Granted, that wasn't off-road but they worked the truck hard and had no problems. Having the exhaust brake really helps when going down grades like those as well. Like I said, I'm not new to towing, trailers, etc. I know the affects of weight, center of gravity, wind resistance, etc. And I know towing a trailer is going to make route planning a little more difficult. That said, there have been very few places I've gone without a trailer where I wouldn't feel comfortable taking one of these trailers and most of those places I wouldn't take a trailer weren't connecting roads but rather out and back roads to places that we didn't end up camping at anyway.
Primary use would be point to point (to point to point ...), any basecamp usage would be for day trips out exploring the local area, etc.
As mentioned in one of my previous posts, we've basically done it all already. The biggest complaints about our current setup are the level of effort to set up and tear down camp and being "stuck" at camp once set up. If we want or have to go somewhere then at the very least the tent has to be packed up. It's not hard work, but it's work. There have been times where we have a long travel day through the midwest and we'll just pull in to a motel and eat the cost because we just don't have the time or energy to find a place to camp and then set the tent up just to tear it back down first thing in the morning to get back on the road. Being able to pull in to a cheap campground or find a dispersed camping spot off the main road and just climb into bed makes things so much easier. Another example was during our recent trip to Montana, my wife had what was likely an allergic reaction to some medication in the middle of the night. It was bad/strange enough that I was thinking about the best way to get her medical attention if needed and how if we had to leave camp in a hurry, either for medical reasons or something like a wildfire, and it was a potential life or death situation then the fastest option would be to just disconnect the roof rack legs and push the RTT off the truck and leave it behind. That would suck for sure and a trailer would alleviate those issues in various ways.
A hard shell RTT would be the cheapest upgrade to the current setup to make actual tent setup easier but that doesn't address the other refinements that we'd like or miss and doesn't address the fact that we'd have to pack up to go anywhere.
Since you're in CO I would assume you've been to the San Juans. Maybe not everywhere there, but some of it. We explored a fair amount of the Alpine Loop area last year and our favorite camp spots were also ones where we would've been able to take the trailer. For example, Bandora Mine and various places off of Last Dollar Rd. We went up to Clear Lake, and while there were camp spots up there that's not a road I'd take a trailer up due to the switchbacks, the width, and the traffic. That would be a great day trip or lunch spot.
My wife and I have spent hours over the past couple of days watching YouTube, reading sites, taking notes, making comparisons, and ultimately we both actually ended up having the same trailer at the top of our list. A lot of it came down to storage, functionality, layout, and overall design. Thinking about where we'd store various things, imagining the steps and motions needing to cook a meal, how inclement weather would affect our ability to do things, and even things like ventilation vs safety with respect to wildlife. For example, the Boreas XT has screen doors but the windows in the main doors are solid. If we wanted airflow then we'd have to keep at least one main door open with the screen door closed. If it started raining or if we thought there might be a bear nearby then we'd have to actually open the screen door and expose ourselves in order to close the main door. That just won't do.
I will say when we first outfit my truck last year the main goal was to start out relatively cheap and simple and get our feet wet. We wanted to see if this kind of travel and experience in general was something we enjoyed, and we really do enjoy it. My wife's initial concern was that we'd do this once (or one major trip) and decide it's not for us or have some other fundamental complaint and then we'd have put all that money into it for nothing, granted these days it's not hard to sell things because of all the supply issues, but regardless she had valid concerns.
As I get older I want less and less to do with people, or rather the public and society, around me. Even staying in developed campgrounds I find unpleasant most of the time. When I think about where I want to travel it's to places where there are no other people, at least not in the immediate vacinity. My wife and I are also in agreement that we'd be perfectly happy living on the road and at some point that will actually be something we could do.
It is also appealing to us that we'd be able to take our animals with us, something we cannot do now. When we travel currently our oldest daughter ends up staying home due to work commitments and taking care of the animals, which she is fine with and doesn't feel like she's really missing out on too much. She also avoids the conflict that is inevitable between her and our other daughter, but that's a whole other can of worms.
So trust me when I say we've experienced a lot and aren't just jumping in blindly. Over the past 4 summers we've traveled somewhere in the neighborhood of 20,000 miles and prior to that we've probably done close to 15,000 miles over a handful of years before we left California. From a normal travel trailer, to a motorhome, to a pop-up trailer, a hybrid trailer, and the RTT we've done a lot, know what we like, what we miss, and what we can easily and happily do without or do differently. I've owned numerous Jeeps and wheeled the Rubicon, Johnson Valley/The Hammers, etc. I've towed nearly everything under the sun short of a 5th wheel or tractor trailer and, not to toot my own horn, have enough experience that I've taken and put trailers most people would never have thought they could go. Our goals and considerations are based on experience and not what we imagine what it might or will be like. Obviously going with an off-road teardrop trailer will be a new experience in and of itself, but we aren't new to any particular aspect of what is involved in doing that. That's why it's largely coming down to what these trailers offer and what they'll enable us to do compared to what we have now. The experiences of cooking outside, or sleeping in a small space, or having to deal with weight and storage space constraints, or figuring out power, solar, and propane requirements are nothing new to us. In fact, I'm pretty certain we, or at least I, do more planning and calculating than a lot of people do. How many folks do you think actually weigh their rigs and make adjustments? How many just eyeball it and think "Well, if it fits and I'm not sitting on the bump stops then I must be fine?" Pretty sure the majority of people out there fall into the latter category. And then we hear about how something is crap because it broke, or it's crap because it's overheating, or it rides like crap, etc.
We know it won't be all sunshine and rainbows, but we're confident that we have a pretty good idea of what we're getting into. :D
Sorry for the novel!