Is it going to make much of a difference to the way the lines are routed on the two options?
I would probably perfer to go through the cooler first before the reservior as it would seem to be kinder to the reservior but have you considered measuring it (got a multimeter with thermocouple input?) to see if its going to make much difference.
Most dry sump lubricating systems are set out the first way too - that way for hill climb cars, they can heat the oil reservior and not have it cooled before going through the engine, enabling the engine to get proper lubrication from limited running.
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