Like GraemeL said, as long as we are not blocking anyone, for an overnighter we leave the trailer hitched. We don't have stabiliser legs, but I do wind down the jockey wheel to take the strain off the back of the tug.
The only time this caught us out was a trip from home, up through Tibooburra, the Santos roads, Dig Tree, camped beside the Arrabury Road, into Welford NP, and finally arrived in Blackall. Hadn't had taken the trailer off once, but as we had propped in the caravan park, I needed to drop it off now.
This is where the fun started. I half heartedly backed the trailer into our spot (was turning in from blind side for some strange reason) and decided that instead of shuffling it around with the tug, I would drop it off and line it up by hand. Dropped the chains and cables and then went to pull the pin out of the Treg, No luck. Took out the WD40 and gave it a good spray, still no luck. It must have been a bit slack in Blackall that day because by now there was a good crowd gathering with chairs and beers to watch. Of course this didn't help my temperament one bit (I still think I was robbed in those anger management classes). Took to the pin with all my strength, crowd cheering, only to see the pin laugh at my efforts. Thinking, thinking, right I will drop the tongue out of the tow bar. This is met with a general murmur of approval and the hiss of another couple of stubbies being opened. Murphy had struck again as I had the tug swung around so far that the tongue wouldn't let go. A general moan escaped from the crowd. No problems, chock the trailer up with the handbrake on and slowly drive forward. I could tell from the sudden start of a Mexican Wave in the crowd that this had been successful. A bit of pushing of the trailer and we were set for the night. The crowd, now robbed of the free entertainment, slowly drifted back to their own vans.
To get the pin out of the hitch, I swung the coupling over 180 and sprayed a lot of WD40 in from the other end and let it soak while we went into town. On return I took out the trusty tent peg alignment tool No.1 (a mash hammer) and gave it a couple of love taps. With a lot of twisting, a fair bit of sweat, and a muttered profanity or two, it finally came free. There had been enough dust and fine grit drop down between pin and hole liner that the WD40 wasn't able to penetrate the mixture by more than half an inch.
All this drama could have been avoided by taking the pin out every day or two, give it a quick wipe and slide it back home, a procedure I have adopted ever since and highly recommend.