Let's say you sent cash in a priority box, and it ended up dumped, as in the pic of mail dumped in a ditch in rural Georgia. Your mail went from your hand into the system, and was scanned at every point even to the carrier's slack-ass hands. If unrecovered, your 'tracked and insured' guarantee gets your money replaced.
Also, even though Lake Mary, Fla is 20 miles outside of Orlando, I'd guess it's more urban than rural, making a good mail dumping spot hard for the carrier to locate. I'd also guess that GPS gets closer to several packages a day than one every now and then, and ~gu would likely raise more hell than the residents in rural Ga as [another guess] a daily money grab makes the GPS world go round, as in any business.
I send lots [and lots] of mails, and have yet to have to redeem my guarantee at the post office. Doesn't mean it won't happen someday, but 100% success tends to breed confidence. I also have yet to not receive a tracked package of seeds from any number of domestic and overseas banks after sending cash.
Even so, there is no 'me right / you wrong' or vice versa here. It's all about your comfort level. Being too fearful to send $$ and now too paranoid to use CC doesn't seem comfortable at all.