OK, how 'bout some technical answers here.
When you 'coast' with the tranny in neutral, the transmission pump is reving at idle speed while the internals are being driven at the coast speed. Not exactly a good idea. The same idea applies in a more extreme case when you tow the vehicle with the rear on the ground. The transmission is not getting lubricant the way it is supposed to.
Depending upon the condition of your transmission, prolonged use like this could lead to premature failure.
This is also not considering the clutch plate slippage that occurs when the transmission is suddenly engaged at speed. Not necessarily fatal, but certainly not good for longevity.