It works great when the trailer is designed properly. Gliders generally have rigging aids, dollies, etc. that when well thought-out, allow them to be assembled and disassembled quickly without damage, and even by one person in some cases. The same could be done for a powered plane, but aircraft, trailer, and rigging aids must be designed with this in mind.
There are also gliders that do get damaged every other time they come out of the trailer, but it's because the trailer is an awkward POS, not because it's in a trailer. Airplanes get damaged in a hangar full of other airplanes, too, you know...