Really interesting thread. 
It occurs to me that OP point 1 essentially deals with who, and point 2 deals with what. There’s been a few posts on when e.g.
What if we contemplate further than a few weeks out - not as far as the next life, but right at the very end of this one. i.e. Instead of
…we consider it as the doctrine of redeath 
. I reckon once is already plenty.
There are people who say ‘dying is just another moment in life like all the others’, but personally I suspect it will seem more significant; the pragmatic thing to do is to prep for it.
From the Taṇhā sutta:
Mendicants, there are these three cravings. What three? Craving for sensual pleasures, craving to continue existence, and craving to end existence.
Unfortunately, even the 3rd option will be no solace on my deathbed because as this guy commented:
I must almost be at the quote quota, but one more:
Because aside from dying in my sleep, I can’t imagine a better state to be in than ‘I’ve let go of everything, am ready to die, but am also ready to (re)live if that turns out to be a thing’. The N8FP appears to be my best option to achieve that goal.