Yeah a lot of cranking will produce excess oil, as Blue says 'the fuel evaporates off'.
The piston acts like a pump and pushes the oil out of the exhaust and carb inlet.
We have to remember the "three"; fuel, compression and spark if one or more of these 3 is not right no amount of cranking will help and as you say, just wear you out, not to mention the excess wear & tear on the starting mechanism.