I'm with you OOT.
I have aerotowed out of some interesting places after 'landing out' - many where the only way to have got the trailer in was by Heli!
I was once landed out in the North island of New Zealand. At the time the Pawnee tug was U/S so, when I knew I was committed to landing I chose a field next to a farm lane for easy access with the trailer.
Upon landing I walked round the field and to my surprise there was no gate in the boundary fence. The crazy Kiwi farmer had a field with no gate and I had managed to land it - bugger! I walked round again to make sure I wasn't losing the plot, but no the field had no gate. I called up the club and told them my predicament and asked they send out quite a few strong blokes as we would have to lift the glider out of the 'paddock' as the locals call it.
Sure enough a while later the cavalry arrive with 6 or 7 blokes to help. The driver takes one look at the field and says " You stupid bloody Pom", then walks over to part of the fence, picks it up and rolls it back to form an opening. " It's a bloody Taranaki fence you dumb s**t". Glider in trailer 5 mins later!
What I did not know then was that the local farmers were often too tight to put in a real gate and just left a part of the fence that could be rolled back then tied up (called a Taranaki fence) - if you looked carefully you could see the hoof marks in the grass where cattle had previously gone through the opening.
As is the custom, the landing out pilot buys his retrieve crew dinner and a beer - bloody expensive landing that was!
Moral of the story (apart from a few negative things about Kiwis) - If you can aerotow out of the field then do so!
I have also had the experience of flying cross country - checking the trailer before flying that is good to go. I ended up landing in a ploughed field (if you are ever tempted to do so don't!) I imagine it is similar to catching an arrestor hook! When the retrieve crew arrived to pick me up they didn't bring the trailer - someone had borrowed the trailer to move something totally unconnected with aircraft and taken it overnight! The trailer thief had gone along the line of trailers till he found one without a glider inside then chose to borrow that one!.
Must be some good landing out stories out there!