Hi, I think you will find a lot of your questions answered here:
http://www.dieselbiker.co.uk/enfield4speedbox.htm
What this box really needs to keep it oil tight is bearings with an O-ring groove on the outside, and shafts with O-ring grooves for the inside of the bearing.
I have fitted two small O rings to the to the main shaft before and after the small sealed bearing. I have also used a small amount of silicone sealant from the top to half way down the side of the small sealed bearing, this will seal on the alloy bulkhead. I always use Loctite bearing fix to stop the bearing from spinning in the housing, this also may keep the oil back. This mod works ok for the right side of the box.
But the problem is the main shaft sleeve, although there is an oil seal, it will leak from this side due to oil passing between the bearing and the sleeve, it travels down the sleeves sprocket grooves (which have been cut too far up the shaft), under the sprocket distance piece (negating the oil seal) and then it drips out between the distance piece and the sprocket / sprocket and nut / tab washer.
Fitting the latest Indian main shaft sleeve, sprocket, and oil seal nut will help a lot.
I also use an oil breather pipe out from the top of the oil filler cap; this stops the excessive build up of air pressure.
My box is a mix of British and Indian and is 100% oil tight. This doesn’t stop the box from having its other problems though.