This is a superb post: very well written, pointing to a skill of extreme importance for every rationalist.

I just want to add my two cents on the modality of grieving.
In my life I've been quite lucky, having had to mourn only the death of my grandparents, of two dogs and one relationship.
All but the last have had little emotional impact on my life: thanks to technology and modern medicine, they happened very slowly, and I feel that I had the time to adjust to a life without those beings, taking a little dose of grief every day until the loss eventually happened.
Losing that relationship instead was much harder. It happen very abruptly, and the woman chose to cut completely the contacts with me afterward. It took me years to process it completely, although the pain subsided in weeks, there was always a process gnarling at the corner of my subconscious. I guess this means there is a kind of inertia, an emotional quality that must be digested, and when it can happen slowly it becomes far easier.