Hi Ben,
That's such horrible news about your friend losing that much money.
The trouble is, it is VERY difficult to buy legitimate Apple products for reselling.
Apple are very picky about who they allow to re-sell their products, and not many eBay sellers make the cut.
For example, they have rules such as the reseller being required to have a brick and mortar store(s) (not just an eBay store) and an annual turnover of $100,000 minimum.
Apple also requires the following before they will even look at you:
* Business license
* General liability insurance certificate
* Photos of each sales location (interior and exterior)
* Tax exemption certificate (if your entity is exempt from state/provincial sales tax)
If you or your friend find a supplier who claims to be able to offer you Apple products without meeting these requirements, run a mile!
I suspect that your friend may have been scammed in a similar situation?
If this is the case, make sure he never buys from a supplier who does not accept a safe payment method such as PayPal or credit card. These are the best payment methods to use, as they provide you with a level of protection if something goes wrong.
For example, if you pay the supplier using credit card, then never hear from them again, or receive the items you ordered, you can inform your bank or credit card provider, and they can do a charge back, and refund you the money you paid them.
Also, try ordering samples from suppliers before you go ahead and make a large order of $500+. This is a good way to determine whether they are legitimate or not.
All the best, I hope your friend finds his feet soon.