G'day Alan,
your modification has some merit. I have worked on heavy diesel engines for some years now whereby engine oil cooling utilising the engines cooling system has been the norm. As stated with the bypass filter arrangement you'd probably have little effect if any in cooling the oil due to lack of flow and volume.
In my opinion you would have to convert the lube system to full flow and have the lube oil passed thru the oil cooler under full lube pressure to achieve any proper amount of heat transfer.
I'd be a bit reluctant to do this for all the engineering and calcs that you would have to do to ensure proper and sufficient oil flow to the engine after modification. One scary point of using the radiator is you may burst the oil cooler in the radiator considering the difference in transmission cooling & lube pressures, and engine lube pressures. A gut full of oil in your cooling system will be big trouble. Whats worse is if you manage to get coolant in your engine oil it can be destructive to engine bearings in a very short amount of time.
There is one bonus though to running the oil through a coolant heat exchanger, and that is you will achieve getting the lube oil to its operating temp in a shorter amount of time.
If your really fixed on oil cooling then I would go to changing the lube system to full flow. Then I would plumb in an oil cooler sandwich adapter with the external oil filter. However with all this I would definitley be making sure that my lube flow rate and pressure would be sufficient for the engine. It may see the need for a higher volume oil pump as well. This may have a flow on effect with extra load on the distributor drive gear, oil pump drive tang, fibre timing gear, etc etc. I think you get my drift of the flow on effect...pardon the pun
Anyway I hope this helps somewhat with your quest. I look forward to seeing what you work out doing.
Cheers
