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The idea of an extend-o tongue is not bad. Forces are not that high comparatively, so something with a screw, for instance, could accomplish that easily. -- Bigger screw for a bigger trailer / load. Stopping would likely be the highest loads (depending on brake balance). Spinning it in and out is no problem with a good gearmotor because it does not have to happen quickly. Cheap GPS and such would make it pretty easy to tell how fast you were going. If the action happened progressively as speed increased from let's say 30 mph (full extension) to 50 mph (full compression) you'd get the bigger benefits at the higher speeds where it's important.
I find it pretty interesting that you mention this, because I've been contemplating the various aspects of doing this for semi trucks for a long time. There are some dynamic issues associated with changing the hitch load as the trailer comes closer, but I think most of those could be properly compensated by axle position and trailer load management (where you put the stuff in/on the trailer).
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