<font color="blue"> If i'm going to run the tractor more in the winter (plowing .5 mile driveway), does it make sense to run synthetic now that the tractor is broken in (400+ hrs)?</font>
Short answer: Yes. Your engine is quite well broken in, and I believe that the superior characteristics of synthetics in cold weather operation, and resultant reduced engine and starter wear, will more than make up for the extra expense of the oil. Seems the jury is still out on whether or not you even need to break in an engine on dino oil before switching to synthetics, but I still prefer to do it. I changed to synthetics after 500 hours, but I waited that long mainly because that's how long it took me to come to my senses, with the able assistance of Skypup, GSXR100 and many others who made too much sense for me to ignore the obvious any longer. Maybe 50 or 100 hours on dino before switching would be "optimal", I really don't know. Just sounds about right.
<font color="blue"> I read that switching to synthetic in vehicles with high mileage may cause some leaks due to the change in viscosity. </font>
My take on the leakage thing is that if your seals and gaskets are in good shape, as yours should be, then they will probably not leak. The leakage "thing", in my opinion, has little or nothing to do with the viscosity of the oil, but rather, with one of the characteristics of synthetics. They are very good at dissolving carbon build-up and sludge of all descriptions, including organic deposits that might be providing a temporary seal to marginally-functioning seals and gaskets, much the same way that Bars-leaks or other cooling system leak-stoppers work. Dissolve the gunk that is temporarily plugging a leak, and the leak will start up again. Don't blame the oil, blame the faulty gasket or seal. Replace them if you start getting leaks after switching to a synthetic, and the leaks will stop. YMMV.