Reconditioned Head, Looking for Smooth Re-start

The new gasket and milling will for sure require resetting the lash, and getting close cold the redoing it warm is a good idea.
Oil on the walls is a good idea, and leaving the plugs out until it makes oil pressure is also a good idea.
I'm sure you will have more opinions on this than you did as to whey the OE gasket went, but this is how I have been doing them for 40 years. :D
(Don't forget a little antiseize for the plug threads.)