1) Yes plus I think he self-cleanses the debuff off every 30 secs or so.
3) I'm inclined to believe so, but we don't use Lightwell
Between Crusader, Lifegiving Gem and Bloodthirst I regen quite a bit of life. BT crits a lot as well, giving me +30 health per tick most of the time. The Heroism trinket I'm not so sure about, it doesn't have a high procrate does it? It'll crit most likely tho, so it might be useful.