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Hey, I was inactive for a long time but I'm still gonna answer your questions now!
About Coup de Grace: I think Last Stand is usually better with Lethal Tempo (and maybe Ghost) if you want to play the "I just run in and attack and hope it will be enough"-playstyle, which is fine but not my style and I think Warwick is better played like this in the top lane and not in the jungle. I like the Press the Attack + Coup de Grace combo because this way you have a tool to get enemys low quickly with PtA (even better with trinity which I play again these days) and then you have the tools to execute them easily with W-Passive, Coup de Grace and PtA %-damage increases. Its just great to quickly kill a carry which I value a lot in the jungle.
About Jak'Sho: The item got significantly nerfed in Season 14 which caused me to not like it that much anymore. It's still a fine option but not what it used to be and I think most other options for a last item are better.
About Shojin: Because of the same reason of me preferring to pick short fights and win them quickly the cdr on basic abilities doesnt give me a lot of value and the other stats ad+health just can't compete with other items for the same price.
About Flash: More playmaking potential (classic early game example is when ganking a lane flash first and instantly Q your target (hold it) and follow their Flash that they will most likely use). Makes you be way more unpredictable than a Warwick just running at you with Ghost. But if you like the "run in and hope for the best"-playstyle more than making cool plays and surprise your enemies then Ghost is probably a good option.
I will update this guide with what I'm doing as soon as possible when the new season hits :)
- Increased damage taken debuff -> team will deal more dmg to your target, too. In jungle you fight with your team a lot
- Juicy burst in combination with Trinity to get enemy below 50% health quickly to trigger W
About your Trinity passive comment: LT takes time to stack, so by the time you have noticeably more attack speed with it the Trinity passive is stacked already anyway + as kind of already mentioned with the faster access to W passive on your target with the extra burst from PTA you often have more attack speed earlier than with LT anyway.
https://app.mobalytics.gg/lol/champions/warwick/build/jungle?buildID=625988237
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It really just depends on what you think is more important in that specific match u're playing. Heal reduce or damage reduction on crits. If they don't have lots of heals definitely take Randuins>Thornmail vs. heavy crit comps. On the other hand, playing versus Soraka (or other heal heavy stuff) it's always Bramble Vest / Thornmail > Randuins.
Anyway, since facing very heavy crit comps is quite rare compared to heal comps you will see yourself buying Bramble Vest far more often than Randuins.
Whether you already got Frozen Heart or not shouldn't really affect your decision here. :)