One of my coworkers used to be a mailman (yes, he actually delivered mail to homes). How he got into insurance is a story best saved for later, but in past conversations, he's told us numerous times that the reason that the Post Office doesn't want you to send cash is that they don't trust postal employees not to steal it. Everyone knows that sorting machines can sometimes be very hard on envelopes and sometimes things arrive already opened. The PO conducts spot checks by sending through cash and seeing if it gets where it was supposed to go intact. According to my coworker, they'll usually do something stupid like not seal the envelope or rip it open themselves revealing the cash.
There's no problem sending cash through the mail, though, if you take basic precautions.
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"They that can give up essential liberty to obtain a little temporary safety deserve neither liberty nor safety." - B. Franklin
"There ought to be limits to freedom." - George W. Bush
"We have met the enemy and he is us." - Pogo
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