Like about 20% of all the users on here I’ve also got a degree in mechanical engineering and if I’m honest it doesn’t help me answer whether or not to grease a headset cup on insertion.
I’ve personally never greased them as they are an interference fit.. but I’m not claiming that is 100% the right thing to do.
I’ve never had a headset cup that has got stuck and can’t remove with a sharp tap of a hammer on a cup removal tool so I’m going to stick to not greasing them.
Can’t prove it “mathematically” but I’d be inclined to think greasing headset cups would make your bike more prone to headset ovalisation as it’s going to aid any micro movements between the cup and frame… I’ve got no evidence of this and it may make no difference, but just a thought. You really want as rigid an interface as possible. It’s not like its a part that gets changed regularly and is at risk of wearing from the fitting and removal, I’d imagine most frames see an average of about 2 headsets in the life of the frame (bearings obviously get changed more).
P.S. There are some good youtube videos that show you how to lace a wheel. That’s the easy bit though, tensioning so you get no egg is the difficult but. Lateral truing is also a piece of cake.