One idea is to T the auto bleeder and incorporate an inline jiggle valve on the bleeder tank return. When air is purged and valve is closed, coolant flows through exchanger. Might just end up using the block drain plug as it is working well on the turbo side and was the OEM solution. Would have better flow and be a bit less "hosey".
I'm not familiar with the auto trans cooling setups but I'm guessing that it pumps oil remotely. I'd rather not run any sort of scavenge pump, so to minimize any engine block oil pump effort, my preference is to bring the coolant to the oil rather than oil to the coolant. It's simpler to implement and a more appealing failure mode.
There are quite a few options that fit. First glance suggests these parts I have should be able to work. I'll know soon enough!