I'm certainly no thermodynamics engineer, but I do know that ethylene glycol/water coolant can absorb and release heat much more efficiently than can engine oil. Cars are cooled by ethylene glycol/water mixtures, not just by engine oil cooling. There's a reason for that....it's more efficient in heat transfer, and it doesn't interfere with the oil circulation demands of the engine.
Pure water cooling would be the most efficient, but water has freeze-point and boiling-point issues, which is why ethylene glycol is used, usually in a 50/50 mix with water. That makes a mix with about 75% of the heat transfer capabilities of plain water, and has a much lower viscosity then does engine oil.
I think that if you were going to do any kind of extended-cooling retrofit, you would be better served by doing what the MoCo did on the Twin Cooled bikes, rather than trying to do it with increased engine oil. As has been pointed out, it would take a lot of R&D to come up with a reliable extended oil-based cooling system that didn't mess up the flow of oil and pressure within the engine, didn't cause sumping issues, etc. And, it still wouldn't transfer heat as efficiently as ethylene glycol/water coolant does.
Ken