At times when I did sell any vehicles in my possession, I always added a licensing fee to the sale, to get the vehicle transferred to the new purchaser.
It was my own terms and condition on the sale agreement. That just eliminated any 'logistics and headache' as experienced by so many when licensing at present.
As the saying goes, don't do deals with family, i was bitten by a family member a few years ago.
I gave, NOT SOLD him my late dads bakkie on the pretext that he sort the registration. Needless to say, a year later, I couldn't get any license's for my cars. He kept the vehicle for few months then sold it off and the new owner didn't transfer the vehicle onto his name.
I gave ZERO F&*KS, I just deregistered the vehicle, paid the outstanding costs associated with this sort of thing moved on.
Good luck OP, you gonna need it!