Not sure that posting "what I would do" is such a good idea as it give all the crooks online a look into your methods.
However I don't believe a fraudster is going to wait that long.
Most of these people just want the cash, so how easy is it to convert your product into cash at a pawn shop?
Is your product something that is targeted by these people?
After you elimimate the professionals then is this a person that wants your product, but can't/won't pay?
One of your problems is having too much empathy for your customer.
This is a business after all.
Would the big boys send out.. No they wouldn't, because they have policies in place that don't rely on emotion.
Does this cause resentment from the customer, sure. But hey its their card thats the problem not yours. Why not have the son pay for it with his card?
I think you will fine however because it probably is a genuine situation.
Maybe you need to make some policies that cover these situations in advance, without the emotion of the moment.
Then you can just say "I would like to help you, But its company policy that....." and not feel too guilty.
Good luck





