G'day Rob,
I had a Hannibal RTT for a year or so and took it through a wide variety of conditions....wet and wild, hot and sticky, dry, dusty and downright freezing. I eventually sold it and got a Mulgo Pop-top on the Defender instead, but I liked it a lot.
As yours is going to be on the box trailer, you've already overcome the foremost disadvantage; that of being unable to drive once you're setup. So, what are the other disadvantages....
Dust and dirt? I didn't find that an issue because when I'm camping, I'm not worried about getting dirty. If the cover is dusty it's only an issue when you put it back on when packing up and are refitting the cover...so let's start there...
Packing up is a pain.
For some reason, the covers are sometimes an awkward fit or the zips seem to want to wreck themselves around the corners, which need dry lube from time to time. I suspect there's a better way...but yeah, this used to be a pain.
Setup. Too much to do.
The essence of the RTT is simplicity and speed of setup....but I found, with the Hannibal at least, that the add-ons such as the window flap stays and the poles for the extension fly to keep the ladder undercover were poorly designed and took too long to setup, all of this exacerbated of course by a 2" lift and me being a shortarse.
Getting up in the night to have a wee.
The ladder is not made for sleepy chaps who have a balance issue due to the beers they had that made them need to get up for a wee in the first place. This used to bug me enough that on cold nights I eventually started getting out onto the front of the roofrack and peeing over the side (passenger side of course, don't tell Mrs Bobby she has no idea...sleeps like roadkill that girl).
Levelling the vehicle.
Not exactly difficult if you have airbags/ maxtracks or similar, but it's another job to do. Worse with a normal ground tent I suppose.
Leaving bedding in the RTT.
Not as simple as you'd think because when you're packing it up, the doona and pillows fall into the middle and everything gets squished. Makes for an unhappy Mrs Bobby because she likes the bed to look nice. Needs bungee cords to keep it down or it all wants folding up before you fold the RTT up.
That's about it. I still rate the RTT as an idea. You're not dealing with a muddy floor or inflatable mattresses, guy ropes and pegs in rocky ground. If you pack up wet, it's super easy to get it out to dry when you get home....assuming you don't need your Landy for an hour or so.
What's the alternative? For me the cheap alternative would be a swag on a groundsheet under the awning or a simple tent + self-inflating mattress.
Fortunately I was in a position to invest in the PopTop so none of these things are an issue anymore. Still miss my swag though, sometimes!


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, but packing it with everything in it was pretty easy with a bit of thought as in where to place stuff.
(we were waiting for the fall
This slows the process somewhat 



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