I think having a trailer would be nice, but I feel it would be used in only 25% of my adventures, which is fine as those times would be with my wife and our travels would be a lot more tame then when I go out with the guys to explore deeper into the back country. (By myself I just sleep inside my rig).
We like ground tenting but there is something to be said about having more room in my rig and a trailer that packed and 80% ready to hitch up and go. Only needing a few things instead of loading up your intire rig.
Some day I'll get my trailer done, (when? maybe when I run out of projects on my rig).
That's definitely my concern/question at this point: will I be able to use it on enough trips to justify the cost. I have sort of two different groups of friends that wheel/camp/Overland/whatever. One group will never do anything I can't take this trailer on. The other group, I don't even know if my Jeep by itself is "enough." I want to go run the Rubicon, mostly because it's been a life-long dream and I live ~1.5 hours from it - but overall I'm sort of done with that type of wheeling at this stage of my life. It's more about getting out in the woods, away from tons of people etc. than it is spending all day to go 2 miles. Back in our more hardcore wheelin' days it wasn't a trip until we spent the better part of a day fixing a broken rig, getting something back on its wheels, and generally MacGyver'in some sort of mess back together.
Now, that just sounds like stress. Will we make it out before dark? Will we even get the broken rig out at all? WTF are we going to do with this rig that is all the way down the hardest trail and totally broken? Etc. Etc. Etc.
My hope is that this trailer means I go out on "simple" Overland type trips way more. Like you said, leave it 80% (or more) packed all the time. There's really no reason I can't have it 100% ready for a trip at all times. It has plenty of room for everything we need to stay in it all times (yes, that means buying dedicated clothes to leave in it - but that's way worth it IMHO). I could leave some jugs of drinking water in it and enough dry goods/food to make it a weekend without even shopping if we really wanted. Sure, most trips we'd stop off and get some groceries to throw in the fridge/freezer for better meals - but it won't be required.
-TJ