I believe the Transfer Request System has some ambiguity and could use an edit to clear things up.
The transfer request should not exceed a value of $500,000 and/or more than 50% of the character's total wealth.
The above statement doesn't make it clear which character's total wealth is in question. Is it the character transferring the items or receiving the items? What about the case where there is a sale of an asset to the other character? If the asset was sold for a fair market price, it's more of a net zero transfer. The example used in the guidelines is for transferring an asset to another character for nothing in return. It seems like the system was put in place more so for helping a new character get started in the game with a little bit of money to buy a vehicle.