Ziggywiggy, the oil leaking out of the hole in the steering shaft is in fact your steering box lube that has been displaced by water leaking past an oring in the steering shaft column. This happened on my Yanmar and resulted in a bearing in the bottom of the steering box having to be replaced. Replaced oring, bearing and lube. Works fine lasts long time.
Very accurately described. Just because our old Yanmars were so well built in MOST areas doesn't mean they were well built in ALL areas. The designs of the steering column, the transmission shifter, the fuel gauge, and the brake covers were pretty much the same across all those old Yanmar models. Your YM1500 is typical.
Anyway, those parts all were made wrong and they all have the same problem: They tend to collect and funnel leak rain/snow water into their working parts. (was it the same designer??) If you have water seeping into any one, you probably have it in all those areas. The good news is that the steering box work is commonly done and is fairly easy and inexpensive to deal with, the tranny is almost bulletproof, you can clean out the fuel tank and even rebuild that clever fuel gauge, and the brakes are just typical drum brake parts There are tricks to each system ranging from "Do this and hope for the best" to complete replacement....as well as everything in between.
If it were me, I'd want to study up on why it happens and what it involves, so at the end of my reply are some diagrams for you to look at.
Just as Spiros says, the "why" is that water seeping into the steering column past the steering wheel mount has no place to go - so instead the water just builds up on top of the steering box seal and gradually infiltrates and displaces the (lighter) steering box oil which then rises into the column. You end up with water in the steering & and oil in the steering column. In the column, as more water enters, it eventually forces the oil to rise up and seep out the improperly placed weep hole. Yes, you guessed it....if the weep hole was where it should be they wouldn't have the problem in the first place. A typical steering box repair involves a top and bottom bearings and a seal. However, you should first start by removing the square head plug in the center top of the steering box, sucking out the oil/water mixture, and filling the box with either light weight grease or 90wt. It will be messy. Don't despair, these are easy near-maintenance kinds of jobs and the tractor itself is a masterpiece.
Check your hydraulic/transmission oil too. If it is milky there has water in the oil.
BTW, simply throwing a tarp over the center of the tractor when not using it will keep 99% of this from ever being a problem....and the seat will last longer too. I do that now; but didn't use to......
Enjoy!
rScotty