I use a tank under the seat as Lewis has suggested, seems to work well although you have to bend down if you want to use it on the move. I nearly crashed once when I hit a pothole, taught me to wait for a well surfaced road. I find sae 50 too thick, I have settled on classic 20-50 as more modern oils are supposed to give clutch slip but I don’t really know.
It’s the thrust bearing which is vulnerable but fortunately the high gear one is on the left near the supply line. Whether pumped oil would get to the RH side I don’t know, it’s obstructed by the thrust rod, oil might just find its way out through the drums. It would be nice to see oil seeping out from the RH side I must admit.
I changed to a different gear to get chain tensions more equal (see technicalities), the old one had done 1000+ miles and the thrust bearings looked fine.
If I am telling you what you already know, my aoplogies,