If he sends it under goods and services, yes.
Friends and fam, no.
Could send two payments of 500
The PayPal rule is for cumulative payments in the course of a year received for Goods& Service; not single transactions. If you receive more than $600 in a year for G&S; you will get a 1099. The threshold was $20k AND 200 transactions.
Same will be applied to EBay sales; I believe