Since you got it with so much oil that it was pouring out, I suspect the previous owner overfilled the crankcase with oil. Drain some of it out, to the middle of the markings on the dipstick (with the dipstick screwed in). The Yanmar 48's are very sensitive to too much oil, and will run like crap if overfilled. If in doubt about the oil quality, change the oil.
If it is truly diesel in the crankcase, it could be the previous owner was trying to clean out the crankcase or something else.
Since you got 280 psi with oil in the cylinder, I suspect either a ring problem (95%) or a leaky valve (5%). Worst case could be a broken ring or piston problem, but that should not be with only 100 hours.
Take off the valve cover, and check the valve clearances with a feeler gauge, per the manual. If the clearances are good, then it's probably a stuck ring problem. You could either fill the cylinder with something like Marvel Mystery oil, and let it soak for a day or two, then suck out the MM oil, and try the compression test or running it again. (Any idea how long this engine had been sitting without being run or cranked)?
The brute force way would be to squirt some oil in there, and if it starts, let it run for a little, then check the compression again.
Remember - Never assume that the previous owner knew what they were doing with this engine. Of the 4 Yanmar's I bought so far, only one of them had a problem, and that was because someone in the previous organization did not follow procedure, and attempted to repair a non existent problem. It usually takes "human input" to destroy one of those little Yanmars. Otherwise they will outlast us.