I do believe you should install a block heater or lower radiator hose heater. I would invest in a small Honda generator for those times when you have no power close. I'd never subject my tractor to cold, dry starts in the winter.
Unless you crank your engine over a couple of minutes before starting you are in effect try starting your engine as far as oil flow I use 100 percent synthetic oil ..have no problem with oil flow...? ....