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The lubrication diagram says there are two oilers on the starter but I can only find one at the end facing the front of the car (see pic).

Where is the second one?

It calls for SAE -30 -- Does 3-in-1 oil work? I have heard that is a 30 weight.

Also, how much to pour in? A couple of drops? Or fill to the top of the hole?

Thanks!

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I wonder if the lube chart is a sort of generic made for all models and maybe is not totally accurate in small details for some cars. Maybe it was worst case. The 356 engines used the gear reduction starter and those have two oilers.

Looking at some Delco info they only show one oiler on starters similar to yours. They do show the two oilers on the reduction types. On yours I think there is only the bushing/bearing at the end cap which gets oil and a bushing at the other end of pinion inside the flywheel space. That bushing might be the oilite kind or permanently greased as they don't expect the flywheel cover be opened.

Only use a couple of drops. If you put in too much, excess oil will get inside and mess up the commutator and brushes. I don't believe 3 in 1 is 30 weight but rather more like 10wt or thinner. It is typically used for very light machinery but would be better than nothing.

Thank you, Howard! Much appreciated.