Hello all,
Does Heartless Intimidator (Breath of the Kami), mill when you take honor or only when an opponent loses honor, these seem to be different enough that it matters especially with Scorpion's stronghold. As if this allows you to continually force mill an opponent it is much stronger, but if it works only on honor loss then it has much fewer triggers?

I was trying to make sure I understood this correctly and am not penalizing the card to much.

Fiveringsdb.com show a developer ruling on the card page which states that yes, it can trigger on taking honor from the opponent as well.

Link to the page: https://fiveringsdb.com/card/heartless-intimidator

A side question...

During the fate phase when dishonored characters leave play, can I trigger an intimidator that is going to leave play as well?

Someone told me that it only works if I am second player, as first player technically goes through that part of the fate phase first.

Yes, that sounds correct. Cards leave play on first player side first, so he wouldn't be around to trigger if you are first player yourself.