I might confuse episodes here and I'm pretty sure he was a butler twice and a guest once.
He got killed by them/her in all 3 timelines (and he survived the 4th? or did he survive the third already, I can't remember. Edit oh yeah, the third time was when he locked himself up @ loli library, that one was fair game.)
When he was a butler, he interacted with them just as much as he did later, but he wasn't as good at his work.
He went to town with Rem, playing with children and made her smile, the viewer at this point most likely thought that she fell for him (when he came up with this demonically possesed talk).
Didn't matter, he would've died from the curse, yet it was Rem who finished him but certainly not out of mercy.
He was *barely* more useful during the time he survived, in fact he seemed to be much more useless to me, he was ill, he couldn't work because he overworked, he made *a lot* of mistakes and troubled them more than anything.
I really think that they did a poor job in developing them. You'd think the time where he went to town with Rem (and got unknowlingly cursed) or the talk with Ram (blue/red ogre story) was just as impactful as his "dedication to work" later on. We have to keep in mind that the battle in the forest happened AFTER the day they went to town together (so he would've been dead before the fight where he proved himself worthy in all other timelines), unless they went 1 day early in what is now the current timeline?
When he was a guest, I thought he handled Rem quite well and what triggered her was his "witch aura", which he never lost/did not have in any of the other timelines. I consider her behavior when he killed Subaru in that timeline crazy. I wasn't refering to her loss of control when she goes berserk.Rem is only batshit crazy when she's in battle mode. That's a logical divide, I think.