Hi Mike,
This project is one of the least fun things you can do. The split pin HAS to come completely out first. As you know, it is down in a deep hole with no working room & there is only a small access hole on one side of the hub. My BN2 takes a 1 1/8" deep socket. If you can get hold of the pin head end, it can be bent to outboard a bit at a time as it is pulled out, & removed from the main center hole without having to exit through the small outer hub hole. It obviously will end up in a C shape. Sometimes, you can grip the pin end with diagonal cutters & lever it out a bit at a time. Standing on your head & doing this in a dark hole can be the height of frustration.
While you are doing this job it would be well to check bearing & seal condition, & adjust the bearing shims per the book, which involves assembling, tightening the nut to somewhere between 40 & 70 ft lbs & checking for no freeplay & no drag. You may need to get extra shims of varying thicknesses to obtain the right fit. The 40 to 70 range should allow one of the split pin holes to line up. I would do this adjusting part with the bearings & parts completely cleaned & not oiled. After the proper shim thickness has been finalized, remove the parts one last time & pack the bearings with WB grease, assemble, tighten the nut, check one last time for proper adjustment, & fight with the split pin to get it back in. Use only one leg of the pin extending fully through the nut & bend it to outboard for easier access the next time.
Note: you may find that the inner spacer & shims have been omitted by someone previously. Or that the outer nuts are not torqued to the proper range. Some folks remove these parts & adjust the bearings as on a more conventional set up. Not good. The Healey spindles are marginally sized & the compressed spacer & shims add greatly to the rigidity of the somewhat weak spindles. The spacers actually add to the effective diameter of the spindles if they are in compression.
And you thought that getting the pin out was the major problem!!!
D
PS: A 1/8" drill bit will just fit the pin diameter.