Tested and unfortunately it seems not to work in that way for DBW 1.71.
Destruction is effective either on map included buildings and on added static objects (the ones with white house icon) only, not also on added stationatry aircrafts (having the red/blue plane icon) and, I guess, on the stationary vehicles (red/blue icon too).
I learned when you are in destruction mode a bridge needs a specifical destruction option (not simply using destruction brush and key "F") using the contextual menu as you point its icon (white one, too). The same is for the generic static objects.
Among the new object pack I have got there is only a couple of generic planes (roughly the Yak-9 and the Bf.109). They could be used to simulate other wrecked planes as in destruction mode they are turned into a mere frame so the aircraft's model is almost not recognizable. Notwithstanding it's impossible to simulate a realistic wrecked jet or even WWII bomber in that way.
In my object package there are a lot of specific (recognizable) train cars, vehicles and tanks wrecked. So I would like to know if the same is possible for the aircraft too.
As stated above, Hunder would you please tell us where could we get those damaged aiplanes you showed?