Anything is possible, just not always realistic.
Oil cooler is usually easy. Bypass it, and run the engine up for a while and see if you get oil out the coolant connections.
Head issues not so, as leaks may only happen under certain conditions, like heating up under high load.
My concern would be you mentioned the bores were scored. That sounds like it's been cooked at some point, so you could be looking at a cracked head or block.
Were the heads pressure tested when off?
Oil cooler is usually easy. Bypass it, and run the engine up for a while and see if you get oil out the coolant connections.
Head issues not so, as leaks may only happen under certain conditions, like heating up under high load.
My concern would be you mentioned the bores were scored. That sounds like it's been cooked at some point, so you could be looking at a cracked head or block.
Were the heads pressure tested when off?