I have completely stripped and rebuilt one of these nice little machines recently. It only had the slow-speed pulley when I got it, but other than being in a sorry state, it was largely intact and original.

Despite being a good design, this drill does have some anomalies around its bearings and lubrication.
The motor bearings in mine were original (1960s Hoffmann). These were of ‘open’ type and would have been ‘greased up’ on assembly. This would have been a right messy thing to do because of the internal end-cover arrangement. There is then no facility to relubricate these motor bearings, so its effectively sealed-for-life.
As a contrast, an excess of grease nipples have been fitted to the spindle head. As you mention, the one of the right feeds into two ball bearings that support the operating lever. Use of two bearings here is a luxury. To give them a relubrication facility as well is quite honestly a little bit OTT. The other two nipples, as you surmise, each feed the pair of quill drive bearings and the spindle bearings.
Regarding the spindle bearings, from everything I have seen, these were always double shielded types which would have had their own controlled-volume grease charge. As this drill unit can run very fast, (up to 18k RPM) it makes no sense to have a relube facility on these bearings. Forcing grease extra grease into double shielded bearings, surrounding them with more grease to stop them purging the excess, then running at high speed is courting disaster.
My quill drive unit contained two open type self-aligning bearings mounted almost side-by-side. (Why this type was used I do not know.) They are significantly bigger than the spindle bearings and therefore at substantially more risk from overheating from uncontrolled greasing. Putting a grease nipple here is just inviting serious trouble.
When I stripped my ‘B’s head, every cavity was chocka-block with grease which was oozing out of every orifice. Some people seem to think that grease just disappears with time. It doesn’t significantly, so eventually, every cc that’s fed in will come out, somewhere. The three units in the head, handle, spindle and quill drive all interconnect too. So if you feed enough grease into say just the quill drive, you will eventually lubricate the handle bearings too!
In my rebuild, I have put ‘sealed-for-life’ bearings in all positions except the handle. The grease inside these bearings will handle the maximum speeds with ease. They will not need any additional grease to be added and will almost certainly out-last me.
The handle bearings were not replaced. I just washed them out and fed them with a few drops of high viscosity oil to produce a nice viscous damped action. I have, as you see in the picture, refitted the three grease nipples. This is just for completeness. I will never use them.
As regards original Herbert guidance on the matter I have trawled the net and can’t find any operators manual, only spare parts guides. I have however seen a picture of a very early ‘B’ which seemed to be fitted with drip-feed oilers! This would actually be a very safe way to lubricate these bearings but unfortunately would make the machine rather messy in use. The nipples fitted to most machines could therefore, as you suggest, have been intended for oil rather than grease.
My feeling though is that Herberts would have subsequently “recommended” grease lubrication (just because it’s a bit more ‘modern’) but would have included strict limits/restrictions on the amount, the type and the frequency. They would have probably suggested things like ‘a No.3 consistency’ (for vertical shafts) ‘Lithium based’ and ‘2 ccs per year’. However, these might have been reasonable for a machine being used for say 5 hours a day, 5 days a week, but in all honesty aren’t really that relevant for intermittent/occasional duty, especially if one doesn’t make use of the 18k RPM speeds.
What you should do now really depends on what’s already in your drill’s bearings. If as was the case with mine, they are already stuffed with lubricants of unknown parentage, I certainly wouldn’t add more. I would either leave as is OR clean it all out and start afresh with oil or new sealed-for-life bearings. It all depends on whether you need another project or not.
As for what all those miscellaneous holes are on the front, I only wish I new! I can only assume it was for some sort of attachment, but I cannot think what.
Gerry