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I would recommend taking Last Stand over Coup de Grace because it provides extra damage on your Alpha Strike. Infact you CAN fight people when you are low hp, you just need to dodge CC (may be harder in low ELOs)
Let me know what you think!
Thanks
Picking Runes is mostly based on enemy champion picks and your own playstyle preference.
Both LT and HOB are working well on Yi but both also have their ups and downs.
If you have trouble deciding on which one to mainly use you should play straight 10 games in a row with the same runes and look, not on how many of those games you've won but on how many of those games you've performed better then with the other runes.
I like to run LT over HOB because HOB only really helps from the early to mid game, thats also when Yi is the weakest but it kinda forces you to do something before it becomes useless while also having an annoying bug in which the runes sometimes does not work after you use Q. LT is more consistent, scales better and makes you get more out of your damage in longer skirmishes. The game is currently going into a direction where consistency again becomes really important and better on Yi, hope that helps.
GL&HF
Now for your Question: (HOB) vs Easy to kill (CONQ) hard to kill, (HOB) squishy enemy comp vs (CONQ) tanky enemy comp, (HOB) Crit/Lethality builds vs (CONQ) On-Hit/Sustain builds. When they have alot of champs which can be hard to kill (3 or more for example) you should aim for onhit and if you think they have enough squishy champs to make the crit/lethality build worth go for that instead. It can also be a matter of what exacly you have to play against for example even if they have alot of hard to kill stuff if they themself don't have the damage and cc to stop you, you can still try to go for crit/lethality (that also counts for the squishys).