69 Barracuda Hemi swap

You might as well do the 392 now. If you do the 5.7 you will have to get a different wiring harness and computer. Also depending on your suspension k frame etc your headers may be different. And if you change transmission harness and ECM will be different. Also if you get a truck 5.7 and switch to a 392 you will have to get a different radiator as the inlet and outlet are different.

I think you are correct if the 5.7 he is running is a pre-Eagle 5.7. But if the 5.7 is '09 or later, seems like he should be able to swap to a 392 with the addition of a wire for the SRV control. I'm kind of planning something similar with my 2017 5.7 swap using a NGC controller and wiring it for the SRV solenoid even though I probably won't have a 6.4 intake to begin with.

At the same time, no idea what kind of mods would need to be done to get the harness to interface with the 8HP90 later on. Might be worth reaching out to Hotwire Auto and ask them if they could build the harness for both at once or something. BTW, the controller Hotwire sells is an aftermarket setup, don't believe anyone had made an A8 swap work using the OEM systems.

Not certain, but I think the only differences between the '08 and down harness and the '09+ is a wire for VCT and probably the crank and cam sensors. Worse case, someone should be able to swap the connectors on the cam and crank plugs (they are all 3 wire I think) and add the 1 VCT wire. And if the harness had the MDS controls and they were deleted, you could just swap one of those at the PCM to the VCT pin and then move a couple of pins at the connector at the back of the cylinder head.